(5S,9R)-indolizidine 209D | 129784-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (5S,9R)-indolizidine 209D
• 英文别名: (5S,9R)-(+)-5-hexylindolizidine；(5S,8aR)-5-hexyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• CAS: 129784-76-5
• 化学式: C₁₄H₂₇N
• 分子量: 209.375
• InChiKey: AXAQOPLJIFRMGI-UONOGXRCSA-N

物化性质

• 沸点：
  265.1±8.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (R)-Undeca-1,10-diene-4,8-diol 在 palladium dihydroxide 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 氢气 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 111.5h， 生成 (5S,9R)-indolizidine 209D
  参考文献：
  名称：

  A Concise Synthesis of (+)-Indolizidine 209D Using a C2-Symmetric 2,6-Diallylpiperidine

  摘要：

  An asymmetric synthesis of (+)-indolizidine 209D (2) using C-2-symmetric 2,6-diallylpiperidine (1) as a chiral building block is presented in a straightforward fashion.

  DOI：

  10.3987/com-05-s(t)15

文献信息

• Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D
  作者：Anil K. Saikia、Kiran Indukuri、Jagadish Das

  DOI：10.1039/c4ob01130a

  日期：——

  A diastereoselective protocol has been established for the synthesis of 4-O-tosyl piperidine containing hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol-6(2H)-one derivatives via the aza-Prins cyclization reaction of cyclic N-acyliminium ions mediated by p-toluene sulphonic acid (p-TSA) under mild conditions. The reaction is highly diastereoselective

  已经建立了非对映选择性的方案，用于合成含有六氢吲哚并嗪-3（2 H）-one，六氢-1 H-喹啉嗪-4（6 H）-one和1,3,4,10b-的4 - O-甲苯磺酰基哌啶四氢吡啶并[2,1-一个]异吲哚-6（2 ħ） -酮衍生物经由环状的氮杂普林斯环化反应ñ通过介导-acyliminium离子p -甲苯磺酸（p -tsa）在温和条件下。该反应是高度非对映选择性的，并产生优异的产率。该方法已应用于吲哚并立定生物碱的有效全合成（±）-Epi-吲哚唑烷167B和209D。
• Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromine
  作者：Manat Pohmakotr、Saisuree Prateeptongkum、Soontorn Chooprayoon、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1016/j.tet.2008.01.008

  日期：2008.3

  (±)-Indolizidines 167B and 209D, their epimers and (±)-tashiromine have been successfully synthesized, starting from simple γ- or α-lactams. The strategy involves the cyclization of α-sulfinyl carbanion onto the carbonyl group of the lactam ring as the key step, leading to the indolizidines containing the phenylsulfinyl group, which are used as precursors for the preparation of the title compounds

  从简单的γ-或α-内酰胺开始，已经成功地合成了（±）-吲哚唑烷167B和209D，它们的差向异构体和（±）-tashiromine。该策略涉及将α-亚磺酰基碳负环到内酰胺环的羰基上的环化作为关键步骤，从而导致含有苯基亚磺酰基的吲哚并咪唑用作制备标题化合物的前体。
• Stereoselective synthesis of (±)-indolizidines 167B and 209D and theirtrans-isomers based on the reductive allylboration of pyridine
  作者：Yu. N. Bubnov、E. V. Klimkina、A. V. Ignatenko

  DOI：10.1007/bf02498166

  日期：1998.5

  intramolecular cyclization oftrans- andcis-2-allyl-6-R-1,2,3,6-tetrahydropyridines, obtained from pyridine and triallylborane, has been elaborated. The closure of the five-membered ring is carried out by hydroboration-oxidation followed by cyclization of the resulting δ-amino alcohols in the presence of the Ph3P−CBr4−Et3N system. (Pr2BH)2 and Pr3B are used as the hydroborating reagents, and H2O2 in an acid medium

  已经详细阐述了基于反式和顺式-2-烯丙基-6-R-1,2,3,6-四氢吡啶的分子内环化合成 5-取代吲哚里西啶的一般方法，该方法从吡啶和三烯丙基硼烷中获得。五元环的闭合是通过硼氢化-氧化然后在 Ph3P-CBr4-Et3N 系统存在下将所得 δ-氨基醇环化来进行的。(Pr2BH)2 和 Pr3B 用作硼氢化试剂，在酸性介质中用 H2O2 氧化形成的 2-[3-(二丙基硼基]-Δ2-哌啶。该方法已用于合成两种天然生物碱类：分别由cis-和trans-2-allyl-6-hexyl-1,2,3,6-tetrahydropiridine制备吲哚里西啶209D（cis-5-hexylindolizidine）及其反式异构体；
• Enantioselective total syntheses of indolizidine alkaloids 167B and 209D
  作者：Richard P. Polniaszek、Stephen E. Belmont

  DOI：10.1021/jo00302a038

  日期：1990.7
• New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor
  作者：Hiroki Takahata、Minoru Kubota、Kozue Ihara、Naoki Okamoto、Takefumi Momose、Nehad Azer、Amira T. Eldefrawi、Mohyee E. Eldefrawi

  DOI：10.1016/s0957-4166(98)00338-3

  日期：1998.9

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.