ethyl 7-O-triflateindole-2-carboxylate | 126260-55-7

• 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 7-O-triflateindole-2-carboxylate
• 英文别名: ethyl 7-(trifluoromethylsulfonyloxy)-1H-indole-2-carboxylate
• CAS: 126260-55-7
• 化学式: C₁₂H₁₀F₃NO₅S
• 分子量: 337.276
• InChiKey: MIXAEYMRYRESCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 7-O-triflateindole-2-carboxylate 在 氢氧化钾 作用下， 生成 7-羟基吲哚-2-羧酸乙酯
  参考文献：
  名称：

  The improved synthesis of 7-oxygenated indoles by Fischer indolization and its application to the first total synthesis of eudistomidin-A

  摘要：

  DOI：

  10.1016/s0040-4039(01)93722-0
• 作为产物：
  描述：

  ethyl (2E)-2-[[2-(trifluoromethylsulfonyloxy)phenyl]hydrazinylidene]propanoate 以52%的产率得到
  参考文献：
  名称：

  MURAKAMI, YASUOKI;TAKAHASHI, HIROYUKI;NAKAZAWA, YOSHIE;KOSHIMIZU, MICHIE;+, TETRAHEDRON LETT., 30,(1989) N6, C. 2099-2100, 1989

  摘要：

  DOI：

文献信息

• Fischer indolization of 2-sulfonyloxyphenylhydrazones: A new and practical approach for preparing 7-oxygenated indoles and application to the first synthesis of eudistomidin-A. (Fischer indolization and its related compounds. Part 28)
  作者：Yasuoki Murakami、Toshiko Watanabe、Hiroyuki Takahashi、Hiroshi Yokoo、Yoshie Nakazawa、Michie Koshimizu、Nori Adachi、Masami Kurita、Tomoko Yoshino、Takayuki Inagaki、Maki Ohishi、Mari Watanabe、Masanobu Tani、Yuusaku Yokoyama

  DOI：10.1016/s0040-4020(97)10255-1

  日期：1998.1

  An efficient method for synthesis of 7-oxygenated indoles was established by Fischer indolization of the phenylhydrazones (10) with a sulfonyloxy group at the ortho-position. This method was applied to the first synthesis of the calmodulin antagonist eudistomidin-A (2).

  通过对在邻位具有磺酰氧基的苯hydr（10）进行费歇尔吲哚化，建立了一种有效的7-氧化吲哚合成方法。该方法被应用于钙调蛋白拮抗剂大毒dist素-A（2）的首次合成。
• Yokoyama, Yuusaku; Takashima, Mitsuru; Higaki, Chitose, Heterocycles, 1993, vol. 36, # 8, p. 1739 - 1742
  作者：Yokoyama, Yuusaku、Takashima, Mitsuru、Higaki, Chitose、Shidori, Kazuko、Moriguchi,Shoko、et al.

  DOI：——

  日期：——
• Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists
  作者：Lionel Kiefer、Floriane Beaumard、Tatiana Gorojankina、Hélène Faure、Martial Ruat、Robert H. Dodd

  DOI：10.1016/j.bmc.2015.12.019

  日期：2016.2

  We report the first comprehensive structure-activity study of calindol (4, (R)-N-[(1H-indol-2-yl) methyl]1-(1-naphthyl) ethanamine), a positive allosteric modulator, or calcimimetic, of the calcium sensing receptor (CaSR). While replacement of the naphthyl moiety of calindol by other aromatic groups (phenyl, biphenyl) was largely detrimental to calcimimetic activity, incorporation of substituents on the 4, 5 or 7 position of the indole portion of calindol was found to provide either equipotent derivatives compared to calindol (e.g., 4-phenyl, 4-hydroxy, 5-hydroxycalindol 44, 52, 53) or, in the case of 7-nitrocalindol (51), a 6-fold more active calcimimetic displaying an EC50 of 20 nM. Unlike calindol, the more active CaSR calcimimetics were shown not to act as antagonists of the closely related GPRC6A receptor, suggesting a more selective profile for these new analogues. (c) 2015 Elsevier Ltd. All rights reserved.
• MURAKAMI, YASUOKI;TAKAHASHI, HIROYUKI;NAKAZAWA, YOSHIE;KOSHIMIZU, MICHIE;+, TETRAHEDRON LETT., 30,(1989) N6, C. 2099-2100, 1989
  作者：MURAKAMI, YASUOKI、TAKAHASHI, HIROYUKI、NAKAZAWA, YOSHIE、KOSHIMIZU, MICHIE、+

  DOI：——

  日期：——
• MURAKAMI, ASUOKI;VATANABEH, TOSIKO
  作者：MURAKAMI, ASUOKI、VATANABEH, TOSIKO

  DOI：——

  日期：——