diethyl (1H-indol-2-ylmethylene)malonate | 65828-72-0

• 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: diethyl (1H-indol-2-ylmethylene)malonate
• 英文别名: 2-Carbethoxy-3-(2-indolyl)-acrylsaeureethylester；Diethyl [(1H-indol-2-yl)methylidene]propanedioate；diethyl 2-(1H-indol-2-ylmethylidene)propanedioate
• CAS: 65828-72-0
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: IFWUEIIMAWQLOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1H-indol-2-ylmethylene)malonate 在 Lipase PS sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 生成 (R)-3-hydroxy-2-(1H-indol-2-ylmethyl)propyl acetate
  参考文献：
  名称：

  Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCβ-selective inhibitors

  摘要：

  Conformationally restricted 3-anilino-4-(3-indolyl)maleimide derivatives were designed and synthesized aiming at discovery of novel protein kinase C beta (PKC beta)-selective inhibitors possessing oral bioavailability. Among them, compounds having a fused five-membered ring at the indole 1,2-position inhibited PKC beta 2 with IC50 of nM-order and showed good oral bioavailability. One of the most potent compounds was found to be PKC beta-selective over other 6 isozymes and exhibited ameliorative effects in a rat diabetic retinopathy model via oral route. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.033
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 丙二酸二乙酯 在 哌啶 作用下， 以 甲苯 为溶剂， 生成 diethyl (1H-indol-2-ylmethylene)malonate
  参考文献：
  名称：

  钯催化的吲哚与乙烯基环氧乙烷的级联烯丙基烷基化和脱芳香化反应†

  摘要：

  我们已经开发了钯催化的分子间的Friedel–Crafts型烯丙基烷基化反应和带有乙烯基环氧乙烷的带有亲核基团的取代吲哚的烯丙基脱芳香化反应，提供了一种在温和条件下合成结构多样的四烃基和螺吲哚烯衍生物的有效方法。

  DOI：

  10.1039/c6ob01523a

文献信息

• FRANKE U.; ROEDER E., ARCH. PHARM. <APBD-AJ>, 1977, 310, NO 12, 975-979
  作者：FRANKE U.、 ROEDER E.

  DOI：——

  日期：——
• Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCβ-selective inhibitors
  作者：Masahiro Tanaka、Shoichi Sagawa、Jun-ichi Hoshi、Fumito Shimoma、Katsutaka Yasue、Minoru Ubukata、Tomoyuki Ikemoto、Yasunori Hase、Mitsuru Takahashi、Tomohiko Sasase、Nobuhisa Ueda、Mutsuyoshi Matsushita、Takashi Inaba

  DOI：10.1016/j.bmc.2006.05.033

  日期：2006.9

  Conformationally restricted 3-anilino-4-(3-indolyl)maleimide derivatives were designed and synthesized aiming at discovery of novel protein kinase C beta (PKC beta)-selective inhibitors possessing oral bioavailability. Among them, compounds having a fused five-membered ring at the indole 1,2-position inhibited PKC beta 2 with IC50 of nM-order and showed good oral bioavailability. One of the most potent compounds was found to be PKC beta-selective over other 6 isozymes and exhibited ameliorative effects in a rat diabetic retinopathy model via oral route. (c) 2006 Elsevier Ltd. All rights reserved.
• Pd-catalyzed cascade allylic alkylation and dearomatization reactions of indoles with vinyloxirane
  作者：Run-Duo Gao、Qing-Long Xu、Li-Xin Dai、Shu-Li You

  DOI：10.1039/c6ob01523a

  日期：——

  We have developed Pd-catalyzed intermolecular Friedel–Crafts-type allylic alkylation and allylic dearomatization reactions of substituted indoles bearing a nucleophilic group with vinyloxirane, providing an efficient method to synthesize structurally diverse tetrahydrocarboline and spiroindolenine derivatives under mild conditions.

  我们已经开发了钯催化的分子间的Friedel–Crafts型烯丙基烷基化反应和带有乙烯基环氧乙烷的带有亲核基团的取代吲哚的烯丙基脱芳香化反应，提供了一种在温和条件下合成结构多样的四烃基和螺吲哚烯衍生物的有效方法。