(5R)-1-[2-(N-Boc-indol-3-yl)ethyl]-5-acetoxymethyl-piperidin-2-one | 255370-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5R)-1-[2-(N-Boc-indol-3-yl)ethyl]-5-acetoxymethyl-piperidin-2-one
• 英文别名: tert-butyl 3-[2-[(5R)-5-(acetyloxymethyl)-2-oxopiperidin-1-yl]ethyl]indole-1-carboxylate
• CAS: 255370-28-6
• 化学式: C₂₃H₃₀N₂O₅
• 分子量: 414.502
• InChiKey: BXDLEUZXYRUJIE-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R)-1-[2-(N-Boc-indol-3-yl)ethyl]-5-acetoxymethyl-piperidin-2-one 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到tert-butyl (3R)-3-(acetyloxymethyl)-3,4,6,7-tetrahydro-2H-indolo[2,3-a]quinolizine-12-carboxylate
  参考文献：
  名称：

  立体控制还原的恶唑基六氢吲哚并[2,3- a ]喹诺嗪衍生物：（+）-塔卡莫宁的不对称全合成

  摘要：

  从对映体纯中间体开始，描述了标题化合物的高效，立体控制的总合成。关键步骤是五环氧杂庚基六氢吲哚并[2,3- a ]喹啉嗪衍生物的非对映选择性催化氢化。

  DOI：

  10.1016/s0040-4039(01)01488-5
• 作为产物：
  描述：

  (2R)-2-(acetoxymethyl)hex-5-en-1-ol 在 吡啶 、 Celite 、 potassium tert-butylate 、 臭氧 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 14.58h， 生成 (5R)-1-[2-(N-Boc-indol-3-yl)ethyl]-5-acetoxymethyl-piperidin-2-one
  参考文献：
  名称：

  Formal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols

  摘要：

  2-Substituted propanediols monoacetates, derived from enzymatic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate 3, useful for the enantioselective synthesis of tacamane alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00434-6

文献信息

• Formal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols
  作者：Bruno Danieli、Giordano Lesma、Silvia Macecchini、Daniele Passarella、Alessandra Silvani

  DOI：10.1016/s0957-4166(99)00434-6

  日期：1999.10

  2-Substituted propanediols monoacetates, derived from enzymatic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate 3, useful for the enantioselective synthesis of tacamane alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled reduction of an oxazepinohexahydroindolo[2,3- a ]quinolizine derivative: asymmetric total synthesis of (+)-tacamonine
  作者：Bruno Danieli、Giordano Lesma、Daniele Passarella、Alessandro Sacchetti、Alessandra Silvani

  DOI：10.1016/s0040-4039(01)01488-5

  日期：2001.10

  Efficient, stereocontrolled total synthesis of the title compound is described, starting from enantiopure intermediates. A key step was the diastereoselective catalytic hydrogenation of a pentacyclic oxazepinohexahydroindolo[2,3-a]quinolizine derivative.

  从对映体纯中间体开始，描述了标题化合物的高效，立体控制的总合成。关键步骤是五环氧杂庚基六氢吲哚并[2,3- a ]喹啉嗪衍生物的非对映选择性催化氢化。