ethyl 3,3-(ethylenedioxy)-4-formylbutyrate | 32296-85-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3,3-(ethylenedioxy)-4-formylbutyrate
• 英文别名: 3,5-Dioxovaleriansaeureethylester-3-ethylenketal；4-Carbethoxy-3-ethylendioxy-butyraldehyd；[2-(2-oxo-ethyl)-[1,3]dioxolan-2-yl]-acetic acid ethyl ester；Ethyl [2-(2-oxoethyl)-1,3-dioxolan-2-yl]acetate；ethyl 2-[2-(2-oxoethyl)-1,3-dioxolan-2-yl]acetate
• CAS: 32296-85-8
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: OAYOREDZDMUDMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3,3-(ethylenedioxy)-4-formylbutyrate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 5.0~60.0 ℃ 、455.96 kPa 条件下， 反应 82.0h， 生成 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one
  参考文献：
  名称：

  Chiral synthesis of the key intermediate of (+)- and (-)-thienamycin

  摘要：

  DOI：

  10.1021/jo00213a025
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 甲苯 、 苯 为溶剂， 反应 25.17h， 生成 ethyl 3,3-(ethylenedioxy)-4-formylbutyrate
  参考文献：
  名称：

  An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: indolizidinone amino acids

  摘要：

  Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide P-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient approach to the enantiopure synthesis of (3S,6S,9S) and (3R,6R,9R) methyl 2-oxo-3-[N-(Boc/Cbz)amino]-1-azabicyclo[4,3,0]nonane-9-carboxylates 1. In this approach, the key intermediates 5a and 5b with different stereochemical configurations were efficiently constructed from the same precursor in high stereoselectivity via asymmetric hydrogenations using (S,S) or (R,R) Et-DUPHOS, Rh(I)-based catalysts. The process, starting from inexpensive diethyl 1,3-acetonedicarboxylate 2, can allow for the practical synthesis of this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00409-9

文献信息

• Total Synthesis of Gelsedilam by Means of a Thiol-Mediated Diastereoselective Conjugate Addition-Aldol Reaction
  作者：You-Ming Huang、Yang Liu、Chang-Wu Zheng、Qiao-Wen Jin、Lu Pan、Ren-Ming Pan、Jun Liu、Gang Zhao

  DOI：10.1002/chem.201604620

  日期：2016.12.19

  The total synthesis of gelsedilam, which features a highly diastereoselective thiol conjugate addition–intramolecular aldol reaction to install the strained and caged [3.2.2] bridged ring system and highly efficient NiCl2/NaBH4‐mediated four‐step transformation in one‐pot to construct its five‐membered lactam ring is reported. The synthesis requires only 18 linear steps from the known compounds, providing

  Gelsedilam的总合成具有高度非对映选择性的硫醇共轭物-分子间羟醛反应，可安装应变和笼状的[3.2.2]桥环系统，并在一锅中高效地进行NiCl 2 / NaBH 4介导的四步转化据报道，构建其五元内酰胺环。合成仅需从已知化合物开始的18个线性步骤，就可以在合成相关的胶体素型生物碱中建立复杂的环系统，并提供了有用的策略。
• Synthetic indole alkaloids. I. Synthesis of a pentacyclic lactam
  作者：Frederick V. Brutcher、William D. Vanderwerff、Barry Dreikorn

  DOI：10.1021/jo00967a024

  日期：1972.1
• Further studies on the synthesis of thienamycin: a facile and stereoselective synthesis of a bicyclic .beta.-keto ester by 1,3-dipolar cycloaddition
  作者：Tetsuji Kametani、Shyh Pyng Huang、Atsushi Nakayama、Toshio Honda

  DOI：10.1021/jo00133a019

  日期：1982.6
• KAMEHTANI, TEHTSUXARU
  作者：KAMEHTANI, TEHTSUXARU

  DOI：——

  日期：——
• An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: indolizidinone amino acids
  作者：Wei Wang、Chiyi Xiong、Victor J Hruby

  DOI：10.1016/s0040-4039(01)00409-9

  日期：2001.4

  Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide P-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient approach to the enantiopure synthesis of (3S,6S,9S) and (3R,6R,9R) methyl 2-oxo-3-[N-(Boc/Cbz)amino]-1-azabicyclo[4,3,0]nonane-9-carboxylates 1. In this approach, the key intermediates 5a and 5b with different stereochemical configurations were efficiently constructed from the same precursor in high stereoselectivity via asymmetric hydrogenations using (S,S) or (R,R) Et-DUPHOS, Rh(I)-based catalysts. The process, starting from inexpensive diethyl 1,3-acetonedicarboxylate 2, can allow for the practical synthesis of this class of compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.