4-(benzylamino)-1-phenylbutan-1-ol | 215391-92-7

• 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: 4-(benzylamino)-1-phenylbutan-1-ol
• CAS: 215391-92-7
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: XTYJIWHZSNKSQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzylamino)-1-phenylbutan-1-ol 在 R-Alpine-Hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成
  参考文献：
  名称：

  Stereocontrol between Remote Atom Centers in Acyclic Substrates. Anti Addition of Hydride to 1,5-, 1,6-, and 1,7-Hydroxy Ketones

  摘要：

  For conformationally unconstrained, acyclic organic compounds, the control of stereogenic centers at remote positions of a chain, that is, at a distance of four or more atom centers, remains a challenging problem in asymmetric synthesis. We report on our studies of 1,5, 1,6, and 1,7 diastereoselectivity in hydride reductions of acyclic hydroxy amino ketones and related compounds, which were sparked by our discovery of high 1,5 diastereocontrol (>10:1) with substrates such as 17 and 23. We have been able to achieve both high 1,5- and 1,6-anti diastereocontrol in the reduction of 1,5- and 1,6-hydroxy ketone substrates, respectively. However, the level of 1,7-anti diastereocontrol with 1,7-hydroxy ketones was only moderate. More specifically, reduction of 23 to 24 with R-alpine-hydride or Zn(BH4)(2) in CH2Cl2 (predominantly) at -78 degrees C gave high 1,5-anti stereoselectivity (anti/syn = 10:1 or 13:1, respectively), and reduction of 34 to 35 with R-alpine-hydride (CH2Cl2) gave high 1,6-anti selectivity (anti/syn = 12:1, respectively), whereas reduction of 46 to 44 with R-alpine-hydride (CH2Cl2) gave only moderate 1,7-anti stereoselectivity (anti/syn = 3:1). Results for reductions of 1,5- and 1,6-hydroxy ketone substrates having the N-benzyl structural subunit replaced (i.e., 27 --> 28, 29 --> 30, 31 --> 32, 52 --> 53, 54a --> 55a, 54b --> 55b, 54c --> 55c, and 56 --> 57) clearly indicate that the stereoelectronic character of this subunit plays a critical. role in the attainment of high anti asymmetric induction. Thus, while we obtained exceptionally high 1,6-anti stereoselectivity in the reduction of the N-mesitylmethyl substrate, 54c, to 1,6-diols 55c (anti/syn = 22:1) with R-alpine-hydride at -78 degrees C in CH2Cl2, the N-methyl substrate, 54b, gave a relatively modest anti/syn ratio of 3:1. The diminished anti/syn ratio of 4:1 in the R-alpine-hydride reduction of methoxy amino ketone 50 to 51 also indicates the importance of the free hydroxyl group for attaining high 1,6-anti stereoselectivity. To rationalize the high remote anti stereocontrol in such acyclic systems, we discuss a chelation-controlled mechanism, involving external hydride addition to a bicyclic metal complex with a coordinated ketone carbonyl (e.g., 33) vs internal hydride addition to a monocyclic metal complex with an uncoordinated ketone carbonyl (e.g., 58).

  DOI：

  10.1021/jo981341m
• 作为产物：
  描述：

  反-苯乙烯乙酸 在 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 4-(benzylamino)-1-phenylbutan-1-ol
  参考文献：
  名称：

  同烯丙基胺和膦硼烷配合物分子内硼氢化的一种机制替代方法

  摘要：

  分子内硼氢化反应从碘活化后的高烯丙基胺硼烷开始。该过程涉及作为中间体的 B-碘硼烷配合物，并且可以通过烯烃内部置换碘化物在生成硼氢化产物的过程中生成阳离子硼烷-烯烃 pi-配合物。该反应可以使用催化量的碘进行。

  DOI：

  10.1021/ja034655m

文献信息

• Acid promoted cyclodehydration of amino alcohols with amide acetal
  作者：Soonho Hwang、Heemin Park、Yongseok Kwon、Sanghee Kim

  DOI：10.1039/c4ra10625c

  日期：——

  A convenient acid-promoted cyclization protocol for the formation of azaheterocycles from amino alcohols is described. The reaction involves the use of N,N-dimethylacetamide dimethyl acetal (DMADA) as the activating reagent of the hydroxyl group. Using this protocol, pyrrolidines or piperidines with various substituents can be synthesized in good to high yields.

  描述了一种方便的酸促进的环化方案，用于从氨基醇形成氮杂杂环。该反应涉及使用N，N-二甲基乙酰胺二甲基乙缩醛（DMADA）作为羟基的活化剂。使用该方案，可以以高产率到高产率合成具有各种取代基的吡咯烷或哌啶。
• [EN] THIOETHER TRIAZOLOPYRIDINE AND TRIAZOLOPYRMIDINE INHIBITORS OF MYELOPEROXIDASE<br/>[FR] INHIBITEURS DE MYÉLOPEROXYDASE À BASE DE THIOÉTHER TRIAZOLOPYRIDINE ET TRIAZOLOPYRMIDINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016040419A1

  公开（公告）日：2016-03-17

  The present invention provides compounds of Formula (I):wherein A, X and Y are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, which may be used as medicaments.

  本发明提供了式（I）的化合物：其中A、X和Y如规范中定义，并包括任何这种新化合物的组合物。这些化合物是髓过氧化物酶（MPO）抑制剂和/或嗜酸性粒细胞过氧化物酶（EPX）抑制剂，可用作药物。
• Amine-Directed Hydroboration: Scope and Limitations
  作者：Matthew Scheideman、Guoqiang Wang、Edwin Vedejs

  DOI：10.1021/ja0774663

  日期：2008.7.1

  Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF•BH3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center

  与使用过量 THF•BH3 的对照实验相比，碘活化诱导高烯丙基和双高烯丙基胺硼烷的分子内硼氢化反应，对区域化学具有良好到出色的控制。氘标记和其他证据证实碘诱导的高烯丙基胺硼烷的硼氢化反应通过与经典 4 中心过程等效的分子内机制发生，并且没有竞争性的逆硼氢化。较长的碳链系链导致较低的区域选择性，而烯丙胺中较短的系链导致转向主要的分子间硼氢化。与碘活化实验相比，THF•BH3 对照实验中烯丙胺硼烷的区域选择性更高，而高烯丙胺硼烷活化则相反。
• Thioether triazolopyridine and triazolopyrimidine inhibitors of myeloperoxidase
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10981879B2

  公开（公告）日：2021-04-20

  The present invention provides compounds of Formula (I): wherein A, X and Y are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, which may be used as medicaments.

  本发明提供了式 (I) 的化合物： 其中A、X和Y如说明书中所定义，以及包含任何此类新型化合物的组合物。这些化合物是髓过氧化物酶（MPO）抑制剂和/或嗜酸性粒细胞过氧化物酶（EPX）抑制剂，可用作药物。
• THIOETHER TRIAZOLOPYRIDINE AND TRIAZOLOPYRMIDINE INHIBITORS OF MYELOPEROXIDASE
  申请人：Bristol-Myers Squibb Company

  公开号：EP3191486A1

  公开（公告）日：2017-07-19