(3S)-N-(tert-Butoxycarbonyl)-3-hydroxy-4-pentenyl-amine | 130192-97-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-N-(tert-Butoxycarbonyl)-3-hydroxy-4-pentenyl-amine
• 英文别名: N-tert-butoxycarbonyl-(3S)-hydroxypent-4-enylamine；(S)-N-t-Butoycarbonyl-3-hydroxy-4-pentenylamine；tert-butyl N-[(3S)-3-hydroxypent-4-enyl]carbamate
• CAS: 130192-97-1
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: NBHOKBUVSSOLQY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-N-(tert-Butoxycarbonyl)-3-hydroxy-4-pentenyl-amine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 乙基溴化镁 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.41h， 生成 N-tert-butoxycarbonyl (-)-Geissman-Waiss lactone
  参考文献：
  名称：

  Alternative Synthesis of (-)-Geissman-Waiss Lactone, a Key Intermediate of Necine Bases

  摘要：

  A facile synthetic route to (-)-Geissman-Waiss lactone, a key intermediate of necine bases, was established by employing ring closing metathesis (RCM), followed by intramolecular Michael reaction of the resulting a,p-unsaturated lactone, as the key steps.

  DOI：

  10.3987/com-05-s(k)29
• 作为产物：
  描述：

  (S)-N-t-Butoycarbonyl-3-acetoxy-4-pentenylamine 在 二异丁基氢化铝 作用下， 生成 (3S)-N-(tert-Butoxycarbonyl)-3-hydroxy-4-pentenyl-amine
  参考文献：
  名称：

  有机溶剂中外消旋3-羟基-4-戊烯基氨基甲酸酯的基于酯交换的酶促拆分

  摘要：

  的纯手性的权宜之计合成ñ -保护的（- [R ）-和（小号）-3-羟基-4- pentenylamines（1和2）已经完成通过外消旋的酶拆分1和2通过在戊烷中固定化脂肪酶介导的。

  DOI：

  10.1016/s0040-4039(00)92080-x

文献信息

• Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine
  作者：Shinji Tanaka、Ramachandran Gunasekar、Tatsuya Tanaka、Yoko Iyoda、Yusuke Suzuki、Masato Kitamura

  DOI：10.1021/acs.joc.7b01181

  日期：2017.9.1

  A new enantioselective catalysis has been developed for the one-step construction of methylene-bridged chiral modules of 1,2- and 1,3-OH and/or NH function(s) from δ- or λ-OH/NHBoc-substituted allylic alcohols and “H2C═O”/“H2C═NBoc”. A protonic nucleophile, either in situ-generated CH2OH or CH2NHBoc, is intramolecularly allylated to furnish eight possible 1,2- or 1,3-O,O, -O,N, -N,O, and -N,N chiral

  已经开发出一种新的对映选择性催化，用于一步合成由δ-或λ-OH/ NHBoc取代的烯丙基的1,2-和1,3-OH和/或NH功能的亚甲基桥式手性模块醇类和“H 2 C = O” /“H 2 C═NBoc”。原位生成的CH 2 OH或CH 2 NHBoc的质子亲核体分子内烯丙基化以提供8种可能的1,2-或1,3-O，O，-O，N，-N，O和-N ，N个具有乙烯基的手性模块，具有高产率和对映选择性。在鞘氨醇的五步合成中已经证明了该方法的实用性。
• Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds
  作者：Hiroki Takahata、Yasunori Banba、Mayumi Tajima、Takefumi Momose

  DOI：10.1021/jo00001a045

  日期：1991.1

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.
• TAKAHATA, HIROKI;BANBA, YASUNORI;TAJIMA, MAYUMI;MOMOSE, TAKEFUMI, J. ORG. CHEM., 56,(1991) N, C. 240-245
  作者：TAKAHATA, HIROKI、BANBA, YASUNORI、TAJIMA, MAYUMI、MOMOSE, TAKEFUMI

  DOI：——

  日期：——
• Transesterification-based enzymatic resolutions of racemic 3-hydroxy-4-pentenylurethanes in organic solvents
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1016/s0040-4039(00)92080-x

  日期：1992.6

  An expedient synthesis of homochiral N-protected (R)- and (S)-3-hydroxy-4-pentenylamines (1 and 2) has been accomplished via the enzymatic resolution of the racemic 1 and 2 mediated by immobilized lipase in pentane.

  的纯手性的权宜之计合成ñ -保护的（- [R ）-和（小号）-3-羟基-4- pentenylamines（1和2）已经完成通过外消旋的酶拆分1和2通过在戊烷中固定化脂肪酶介导的。
• Alternative Synthesis of (-)-Geissman-Waiss Lactone, a Key Intermediate of Necine Bases
  作者：Toshio Honda、Sae Matsumoto

  DOI：10.3987/com-05-s(k)29

  日期：——

  A facile synthetic route to (-)-Geissman-Waiss lactone, a key intermediate of necine bases, was established by employing ring closing metathesis (RCM), followed by intramolecular Michael reaction of the resulting a,p-unsaturated lactone, as the key steps.