ethyl (3R)-2-ethoxycarbonyl-3-[3-(5-methylindolyl)]-3-phenyl-propanoate

• 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: ethyl (3R)-2-ethoxycarbonyl-3-[3-(5-methylindolyl)]-3-phenyl-propanoate
• 英文别名: diethyl 2-((5-methyl-1H-indol-3-yl)(phenyl)methyl)malonate；(R)-ethyl 2-ethoxycarbonyl-3-[3-(5-methylindolyl)]-3-phenylpropanoate；diethyl 2-[(R)-(5-methyl-1H-indol-3-yl)-phenylmethyl]propanedioate
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: SOROOHUOWYFDMB-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二酸二乙酯 在 ammonium cerium (IV) nitrate 、 [bis(4-ethoxyphenyl)-[(2S)-pyrrolidin-2-yl]methoxy]-trimethylsilane 作用下， 以 乙醇 为溶剂， 反应 61.33h， 生成 ethyl (3R)-2-ethoxycarbonyl-3-[3-(5-methylindolyl)]-3-phenyl-propanoate
  参考文献：
  名称：

  丙二酸酯与α,β-不饱和醛的环保不对称有机催化共轭加成：在手性吲哚合成中的应用

  摘要：

  目前，合成社区面临着解决日益增长的环境问题的需要。为了减少有机转化对环境的影响，所有传统的合成方法，包括不对称合成方案，都应该进行审查，如果可能的话，由继续满足效率、选择性需求的新工艺取代，但对环境无害。

  DOI：

  10.1002/ejoc.201300431

文献信息

• Sidearm Effect:  Improvement of the Enantiomeric Excess in the Asymmetric Michael Addition of Indoles to Alkylidene Malonates
  作者：Jian Zhou、Yong Tang

  DOI：10.1021/ja026936k

  日期：2002.8.1

  A pseudo-C3-trisoxazoline was designed and synthesized. The improvement of the traditional bisoxazoline into a novel trisoxazoline by a sidearm approach resulted in highly catalytic enantioselective Michael addition of indoles to alkylidene malonates. Excellent catalytic reactivity and enantioselectivity (up to 99% yield and 93% ee) were achieved.

  设计并合成了假-C3-三恶唑啉。通过侧臂方法将传统的双恶唑啉改进为新型三恶唑啉导致吲哚与亚烷基丙二酸酯的高度催化对映选择性迈克尔加成。实现了优异的催化反应性和对映选择性（高达 99% 的产率和 93% 的 ee）。
• Enantioselective Friedel–Crafts reaction of indoles with arylidene malonates catalyzed byⁱPr-bisoxazoline–Cu(OTf)₂
  作者：Jian Zhou、Yong Tang

  DOI：10.1039/b313197a

  日期：——

  The cheap and simple iPr-bisoxazoline–Cu(OTf)2 proves to be an efficient catalyst in the asymmetric Friedel–Crafts reaction of indole with arylidene malonates. In iBuOH, the S-enantiomer was obtained in up to 97% ee, while the opposite enantiomer was obtained in up to 78% ee in CH2Cl2 or TTCE.

  便宜且简单的 iPr-bisoxazoline–Cu(OTf)2 证明在吲哚与芳基烯丙烯酸酯的非对称 Friedel–Crafts 反应中是一种有效的催化剂。在 iBuOH 中，获得了高达 97% 的 S-对映体，而在 CH2Cl2 或 TTCE 中获得的相反对映体则高达 78% ee。
• Synthesis of New C2- Symmetric Fluoren-9-ylidene Malonate Derived Bis(oxazoline) Ligands and Their Application in Friedel-Crafts Reactions
  作者：Jing Li、Hong-Liang Chen、Lei Liu、Bin Fu

  DOI：10.3390/molecules15128582

  日期：——

  series of new C(2)-symmetric fluoren-9-ylidene malonate-derived bis(oxazoline) ligands were synthesized from fluoren-9-ylidene malonate and enantiomerically pure amino alcohols via a convenient route. Their asymmetric catalytic properties in the Friedel-Crafts reactions of indoles with arylidene malonates were evaluated, and the Cu(OTf)2 complex of a fluoren-9-ylidene malonate-derived bis(oxazoline) bearing

  一系列新的 C(2)-对称芴 9-ylidene 丙二酸酯派生的 bis(oxazoline) 配体是通过方便的路线从芴 9-ylidene 丙二酸酯和对映体纯氨基醇合成的。评估了它们在吲哚与亚芳基丙二酸酯的 Friedel-Crafts 反应中的不对称催化性能，并且带有苯基的芴-9-亚基丙二酸酯衍生的双（恶唑啉）的 Cu(OTf)2 络合物显示出中等至良好的对映选择性。高达 88% ee）。
• Synthesis of heteroarylidene malonate derived bis(thiazolines) and their application in the catalyzed Friedel–Crafts reaction
  作者：Lei Liu、Jing Li、Mingan Wang、Fengpei Du、Zhaohai Qin、Bin Fu

  DOI：10.1016/j.tetasy.2011.03.003

  日期：2011.3

  A series of novel heteroarylidene malonate derived bis(thiazoline) ligands 1 and 2 were synthesized and applied to a Friedel-Crafts reaction between indole and alkylidene malonate. The Cu(OTf)(2) complex of ligand 2b bearing a benzyl group afforded moderate to excellent enantioselectivity for the adducts (up to >99% ee). (C) 2011 Elsevier Ltd. All rights reserved.
• An Eco-Friendly Asymmetric Organocatalytic Conjugate Addition of Malonates to α,β-Unsaturated Aldehydes: Application on the Synthesis of Chiral Indoles
  作者：Karla Santos Feu、Anna Maria Deobald、Senthil Narayanaperumal、Arlene G. Corrêa、Márcio Weber Paixão

  DOI：10.1002/ejoc.201300431

  日期：2013.9

  synthetic community faces the need to ad-dress growing environmental concerns. To lessen the envi-ronmental impact of organic transformations, all conven-tional synthetic methodologies, including asymmetric syn-thetic protocols, should be reviewed and, if possible, re-placed by new processes that continue to meet the needs ofefficiency, selectivity but that are environmentally benign.

  目前，合成社区面临着解决日益增长的环境问题的需要。为了减少有机转化对环境的影响，所有传统的合成方法，包括不对称合成方案，都应该进行审查，如果可能的话，由继续满足效率、选择性需求的新工艺取代，但对环境无害。