N-(benzyloxycarbonyl)dipropylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzyloxycarbonyl)dipropylamine
• 英文别名: benzyl dipropylcarbamate；benzyl N,N-dipropylcarbamate
• 化学式: C₁₄H₂₁NO₂
• mdl: MFCD30258350
• 分子量: 235.326
• InChiKey: NJZUPPHIKMMTTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二烯丙基胺 在 palladium on activated charcoal 二苯硫醚 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 91.0h， 生成 N-(benzyloxycarbonyl)dipropylamine
  参考文献：
  名称：

  Pd / C催化的化学选择性加氢方法，使用二苯硫作为合理的催化剂毒物

  摘要：

  尽管Pd / C是最有用的加氢催化剂之一，但Pd / C的高催化剂活性导致难以将其应用于不同类型的可还原官能团之间的化学选择性加氢。为了实现使用Pd / C进行化学选择性加氢，我们研究了催化剂毒物作为催化剂活性的控制剂。我们发现，向Pd / C催化的氢化反应混合物中添加Ph 2 S（二苯硫醚）可导致Pd / C合理失活。通过使用Pd / C–Ph 2 S催化体系，烯烃，乙炔和叠氮化物可以选择性地还原成芳族羰基，芳族卤化物，氰基，苄基酯和N-Cbz（苄氧羰基）保护基。本方法有望作为合成有机化学中通用和实用的化学选择性加氢方法。

  DOI：

  10.1016/j.tet.2006.09.094

文献信息

• Chemoselective Hydrogenation Catalyzed by Pd on Spherical Carbon
  作者：Hiroyoshi Esaki、Tomohiro Hattori、Aya Tsubone、Satoko Mibayashi、Takao Sakata、Yoshinari Sawama、Yasunari Monguchi、Hidehiro Yasuda、Kazuto Nosaka、Hironao Sajiki

  DOI：10.1002/cctc.201300639

  日期：2013.12

  developed a highly chemoselective hydrogenation method using a novel palladium catalyst supported on spherical carbon (0.5 % Pd/SC). The 0.5 % Pd/SC exhibited a novel catalytic activity and could achieve the chemoselective hydrogenation of alkynes, alkenes, azides, nitro groups, and aliphatic O‐tert‐butyldimethylsilyl (TBS) ethers without hydrogenolysis of benzyl esters, benzyl ethers, nitriles, aromatic

  我们已经开发出了一种新型的高化学选择性氢化方法，该方法使用了一种新型的负载在球形碳（0.5％Pd / SC）上的钯催化剂。的0.5％的Pd / SC显示出新颖的催化活性，并可能实现炔烃，烯烃，叠氮化物，硝基基团的化学选择性氢化，以及脂族ö -叔丁基二甲基（TBS）醚无苄基酯，苄基醚，腈的氢解，芳族酮，N-碳苄氧基（N- Cbz）保护基和芳族O- TBS醚。
• Novel Palladium-on-Carbon/Diphenyl Sulfide Complex for Chemoselective Hydrogenation: Preparation, Characterization, and Application
  作者：Akinori Mori、Tomoteru Mizusaki、Masami Kawase、Tomohiro Maegawa、Yasunari Monguchi、Shinobu Takao、Yukio Takagi、Hironao Sajiki

  DOI：10.1002/adsc.200700571

  日期：2008.2.22

  Pd/C[Ph2S], was developed to achieve the highly chemoselective hydrogenation of alkenes, acetylenes, azides, and nitro groups in the presence of aromatic ketones, halides, benzyl esters, and N-Cbz protective groups. Instrumental analyses of the heterogeneous catalyst demonstrated that diphenyl sulfide was embedded on Pd/C via coordination of its sulfur atom to palladium metal or physical interaction with graphite

  开发了一种固定在钯碳体系上的二苯硫醚Pd / C [Ph 2 S]，以在芳族酮，卤化物，苄基酯存在下实现烯烃，乙炔，叠氮化物和硝基的高化学选择性氢化。和N-Cbz保护基。对非均相催化剂的仪器分析表明，二苯硫醚通过其硫原子与钯金属的配位或与活性炭石墨层的物理相互作用而嵌入Pd / C中。催化剂可被回收并重复使用至少五次，而反应活性没有任何显着损失。
• [EN] TRIAZOLE COMPOUNDS FOR THE TREATMENT OF DYSMENORRHOEA<br/>[FR] COMPOSES TRIAZOLE POUR LE TRAITEMENT DE LA DYSMENORRHEE
  申请人：PFIZER LTD

  公开号：WO2004037809A1

  公开（公告）日：2004-05-06

  A compound of formula (I), a pharmaceutically acceptable salt or solvate thereof, wherein R' represents C,-C6 alkyl, -(CH2)c-[C3-C8 cycloalkyl]-, -(CH2)C -W or -(CH2)C-Z-(CH2)dW; W represents C1-C6 alkyl, C1-C6 alkyloxy, -C02[C1-C6 alkyl], -CONR4R5, an optionally substituted phenyl group, NR4R5, het2 or het3; Z represents O or S(O)g; g represents 0, 1 or 2; R2 represents a phenyl group, optionally fused to a 5- or 6- membered aryl or heterocyclic group which may contain one or more heteroatoms selected from N, O or S; the phenyl group and the optionally fused group being optionally substituted; Ring A represents a 4-, 5- or 6- membered saturated heterocyclic group containing at least one N; Ring B represents a phenyl group or het1, each group being optionally substituted; R7 independently represents H1 C1-C6 alkyl, OR3, -(CH2)e-R3 or -(CH2)f-O-(CH2)e-R3; at each occurrence R3 independently represents H1 C1-C6 alkyl optionally substituted by Y, -(CH2)g [C3-C8 cycloalkyl], phenyl, benzyl, pyridyl or pyrimidyl; at each occurrence R4 and R5 independently represent H1 Cl-C6 alkyl (optionally substituted with Cl-C6 alkyloxy), (CH2)gC02-[C1-C6 alkyl], -S02Me, -(CH2)g [C3-C8 cycloalkyl], S02Me, phenyl, benzyl, pyridyl or pyrimidyl; or R4 and R5 together with the N atom to which they are attached represent a heterocyclic group of from 3 to 8 atoms; Y independently represents a phenyl group, NR4R5 or het4, the phenyl group being optionally substituted; het1 represents a 4-, 5- or 6- membered saturated, or unsaturated, heterocyclic group containing at least one N (but which may also contain one or more O or S atoms); het2 and het4 represent an optionally substituted 4-, 5-, 6- or 7- membered saturated, or unsaturated, heterocyclic group containing at least one N (but which may 5 also contain one or more O or S atoms); het3 represents an optionally substituted 4-, 5-, 6- or 7- membered saturated, or unsaturated, heterocyclic group containing at least one O (but which may also contain one or mare N or S atoms); at each occurrence R6 independently represents H1 C1-C6 alkyl optionally substituted by Y, =(CH2)g [C3-C8 cycloalkyl], phenyl, benzyl, pyridyl or pyrimidyl; a and b independently represent 0 or 1; c,, d, a end g independently represent 0, 1, 2, 3 or 4; . f índeperldently represents 1, 2, 3 or 4; provided that: (i) a + b cannot equal 0; and províded,that,when R1 represents -(CH2)c-Z-(CH2)d-W and W represents.NR4R5 or any N linked heterocyclic, group then d must not be, 0 or 1; and (iii), provided that when R2 represents a phenyl group substituted by a group of, formula -(CH2)eOR3, -(CH2)e-OCOR3 or -(CH2)e,OCOR3 ;or het1,and/or het2 are substituted by a group of formula -(CH2)eOR3, (CH2),-CO2R3 or -(CH2)eOCOR3; or when R7 represents -OR3 or -(CH2)f-0-(CH2)e-R3 and e is 0; or when W represents a phenyl group substituted with -OR

  式(I)的化合物，其药学上可接受的盐或溶剂，其中R'代表C1-C6烷基，-(CH2)c-[C3-C8环烷基]-，-(CH2)C-W或-(CH2)C-Z-(CH2)dW；W代表C1-C6烷基，C1-C6烷氧基，-C02[C1-C6烷基]，-CONR4R5，一个可选择取代的苯基，NR4R5，het2或het3；Z代表O或S(O)g；g代表0、1或2；R2代表一个苯基，可选择与含有一个或多个异原子N、O或S的5-或6-成员芳基或杂环基融合；苯基和可选择融合的基团可选择取代；环A代表至少含有一个N的4-、5-或6-成员饱和杂环基；环B代表一个苯基或het1，每个基团可选择取代；R7独立地代表H1 C1-C6烷基，OR3，-(CH2)e-R3或-(CH2)f-O-(CH2)e-R3；在每次出现时，R3独立地代表H1 C1-C6烷基，可选择由Y取代，-(CH2)g[C3-C8环烷基]，苯基，苄基，吡啶基或嘧啶基；在每次出现时，R4和R5独立地代表H1 Cl-C6烷基（可选择用Cl-C6烷氧基取代），(CH2)gC02-[C1-C6烷基]，-S02Me，-(CH2)g[C3-C8环烷基]，S02Me，苯基，苄基，吡啶基或嘧啶基；或R4和R5与它们连接的N原子一起代表3到8个原子的杂环基；Y独立地代表一个苯基，NR4R5或het4，苯基可选择取代；het1代表至少含有一个N的4-、5-或6-成员饱和或不饱和杂环基（但也可能含有一个或多个O或S原子）；het2和het4代表一个可选择取代的4-、5-、6-或7-成员饱和或不饱和杂环基，至少含有一个N（但也可能含有一个或多个O或S原子）；het3代表一个可选择取代的4-、5-、6-或7-成员饱和或不饱和杂环基，至少含有一个O（但也可能含有一个或多个N或S原子）；在每次出现时，R6独立地代表H1 C1-C6烷基，可选择由Y取代，=(CH2)g[C3-C8环烷基]，苯基，苄基，吡啶基或嘧啶基；a和b独立地代表0或1；c、d、a和g独立地代表0、1、2、3或4；f独立地代表1、2、3或4；条件是：(i) a+b不能等于0；并且，条件是，当R1代表-(CH2)c-Z-(CH2)d-W且W代表NR4R5或任何N连接的杂环基时，d不能为0或1；以及(iii)，条件是，当R2代表一个苯基，被-(CH2)eOR3，-(CH2)e-OCOR3或-(CH2)e-OCOR3取代；或het1和/或het2被-(CH2)eOR3，(CH2)e-CO2R3或-(CH2)eOCOR3取代；或当R7代表-OR3或-(CH2)f-O-(CH2)e-R3且e为0时；或当W代表一个被-OR取代的苯基时。
• Palladium-supported ionic liquid catalyst (Pd-SH-SILC) immobilized on mercaptopropyl silica gel as a chemoselective, reusable and heterogeneous catalyst for catalytic hydrogenation
  作者：Hisahiro Hagiwara、Tomomi Nakamura、Takashi Hoshi、Toshio Suzuki

  DOI：10.1039/c1gc15217c

  日期：——

  Palladium acetate was immobilized as Pd-SH-SILC (Pd-supported ionic liquid catalyst) in the pores of amorphous mercaptopropyl silica gel with the aid of an ionic liquid [bmim]BF4. The heterogeneous Pd-SH-SILC was effective for catalytic hydrogenation of a variety of olefins at atmospheric pressure and room temperature. It withstood recycling up to 10 times by decantation.

  醋酸钯 被固定为Pd-SH-SILC（Pd支持 离子液体 催化剂借助无定形巯基丙基硅胶的孔 离子液体[bmim] BF 4。异质Pd-SH-SILC对催化有效氢化 各种 烯烃在大气压和室温下。通过倾析，它可以承受多达10次的回收利用。
• Reduction of Carbon−Carbon Double Bonds Using Organocatalytically Generated Diimide
  作者：Christian Smit、Marco W. Fraaije、Adriaan J. Minnaard

  DOI：10.1021/jo801588d

  日期：2008.12.5

  An efficient method has been developed for the reduction of carbon-carbon double bonds with diimide, catalytically generated in situ from hydrazine hydrate. The employed catalyst is prepared in one step from riboflavin (vitamin B(2)). Reactions are carried out in air and are a valuable alternative when metal-catalyzed hydrogenations are problematic.

  已经开发出一种有效的方法来用二酰亚胺还原碳-水双键，二酰亚胺是由水合肼原位催化生成的。所用的催化剂是从核黄素（维生素B（2））一步制备而成的。反应是在空气中进行的，当金属催化的加氢反应有问题时，它是一种有价值的替代方法。