2-氰基-2-(3-噻吩基)乙酸乙酯 | 21418-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 2-氰基-2-(3-噻吩基)乙酸乙酯
• 英文名称: ethyl thien-3-ylcyanoacetate
• 英文别名: ethyl 3-thienyl-α-cyanoacetate；Ethyl 2-cyano-2-(3-thienyl)acetate；ethyl 2-cyano-2-thiophen-3-ylacetate
• CAS: 21418-54-2
• 化学式: C₉H₉NO₂S
• mdl: MFCD03412584
• 分子量: 195.242
• InChiKey: BXETXHHTOKRXCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氰基-2-(3-噻吩基)乙酸乙酯 在 盐酸 作用下， 以 水 为溶剂， 生成 (3-噻吩基)丙二酸二乙酯
  参考文献：
  名称：

  Preparation of a 3-thienylmalonic acid and the corresponding diesters

  摘要：

  在极性溶剂中，在铜(I)卤化物的存在下，反应具有以下公式的噻吩化合物制备3-噻吩丙二酸或其二酯：其中X=I或Br，R.sub.1=H或C.sub.1-4烷基，R.sub.2=H或C.sub.1-2烷基，R.sub.3=H或C.sub.1-2烷基，但R.sub.2和R.sub.3不能同时是烷基，与具有以下公式的单去质子亚甲基化合物反应：其中存在阳离子且Z'=Z"为CN或COOR，其中R为C.sub.1-4烷基，或Z'=CN且Z"=COOR'，其中R'为C.sub.1-2烷基，随后通过已知方法水解以获得相应的游离酸。

  公开号：

  US04262129A1

文献信息

• 3-Thienylmalonic acids, the corresponding diesters and their preparation
  申请人：Océ-Andeno B.V.

  公开号：EP0002846A1

  公开（公告）日：1979-07-11

  Preparation of a 3-thienylmalonic acid or a diester thereof comprising reacting in a polar solvent in the presence of a copper (I) halide a thiophene compound of formula: wherein X = I or Br R1 = H or a C1-4 alkyl group R2 = H or a C1-2 alkyl group R3 = H or a C1-2 alkyl group with the proviso that R2 and R3 cannot be an alkyl group simultaneously, with a mono-deprotonated methylene compound of formula: wherein Z' = Z" is CN or COOR in which R is a C1-4 alkyl group, or Z' = CN and Z" = COOR' in which R' is a C1-2 alkyl group followed by hydrolysis by methods known per se to get the corresponding free acid.

  制备 3-噻吩丙二酸或其二酯，包括在极性溶剂中，在卤化铜（I）的存在下，使 式中的噻吩化合物发生反应： 式中 X = I 或 Br R1 = H 或 C1-4 烷基 R2 = H 或 C1-2 烷基 R3 = H 或 C1-2 烷基 在 R2 和 R3 不能同时为烷基的条件下，与式中的单质子化亚甲基化合物反应： 其中 Z' = Z" 是 CN 或 COOR（其中 R 是 C1-4 烷基），或 Z' = CN 和 Z" = COOR'（其中 R' 是 C1-2 烷基），然后用本身已知的方法进行水解，得到相应的游离酸。
• Managing Highly Coordinative Substrates in Asymmetric Catalysis: A Catalytic Asymmetric Amination with a Lanthanum-Based Ternary Catalyst
  作者：Tomoyuki Mashiko、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja9052653

  日期：2009.10.21

  Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)(3)center dot 6H(2)O, (R)-3a and H-D-Val-V'Bu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)(3)center dot 6H(2)O/(R)-3a/H-D-Val-O'Bu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted alpha-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to > 99% yield and > 99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.
• US4252976A
  申请人：——

  公开号：US4252976A

  公开（公告）日：1981-02-24
• US4262129A
  申请人：——

  公开号：US4262129A

  公开（公告）日：1981-04-14
• Preparation of a 3-thienylmalonic acid and the corresponding diesters
  申请人：Oce-Andeno B.V.

  公开号：US04262129A1

  公开（公告）日：1981-04-14

  Preparation of a 3-thienylmalonic acid or a diester thereof comprising reacting in a polar solvent in the presence of a copper (I) halide a thiophene compound of formula: ##STR1## wherein X=I or Br, R.sub.1 =H or a C.sub.1-4 alkyl group, R.sub.2 =H or a C.sub.1-2 alkyl group and R.sub.3 =H or a C.sub.1-2 alkyl group, with the proviso that R.sub.2 and R.sub.3 cannot be an alkyl group simultaneously, with a mono-deprotonated methylene compound of formula: ##STR2## wherein a cation is present and Z'=Z" is CN or COOR in which R is a C.sub.1-4 alkyl group, or Z'=CN and Z"=COOR' in which R' is a C.sub.1-2 alkyl group, followed by hydrolysis by methods known per se to get the corresponding free acid.

  在极性溶剂中，在铜(I)卤化物的存在下，反应具有以下公式的噻吩化合物制备3-噻吩丙二酸或其二酯：其中X=I或Br，R.sub.1=H或C.sub.1-4烷基，R.sub.2=H或C.sub.1-2烷基，R.sub.3=H或C.sub.1-2烷基，但R.sub.2和R.sub.3不能同时是烷基，与具有以下公式的单去质子亚甲基化合物反应：其中存在阳离子且Z'=Z"为CN或COOR，其中R为C.sub.1-4烷基，或Z'=CN且Z"=COOR'，其中R'为C.sub.1-2烷基，随后通过已知方法水解以获得相应的游离酸。