ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate | 76985-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate
• 英文别名: Ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropane carboxylate；ethyl 2-(1,3-benzodioxole-5-carbonyl)-3-(3,4,5-trimethoxyphenyl)cyclopropane-1-carboxylate
• CAS: 76985-19-8
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: KCWXIJVHIDUEEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate 生成 ethyl (5R,6R)-8-oxo-5-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[f][1,3]benzodioxole-6-carboxylate
  参考文献：
  名称：

  VYAS, DOLATRAL M.;SKONEZNY, PAUL M.

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (dimethylsulfuranylidene)acetate 、 (E)-1-Benzo[1,3]dioxol-5-yl-3-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以80%的产率得到ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropanecarboxylate
  参考文献：
  名称：

  串联氧化工艺，用于制备功能化的环丙烷。

  摘要：

  [反应：见正文]已经开发了一种新颖的二氧化锰介导的串联氧化工艺（TOP），该工艺可以将烯丙醇直接转化为环丙烷，中间醛被稳定的硫内酯原位捕获。此方法已成功应用于各种烯丙醇和简单，天然存在的木脂素（+/-）-picropodophyllone的正式合成。

  DOI：

  10.1021/ol0483394

文献信息

• Trapping the intermediate involved in the intramolecular cyclisation of cyclopropyl ketones. A convenient preparation of open-chain γ-hydroxy ketones
  作者：William S. Murphy、Sompong Wattanasin

  DOI：10.1016/s0040-4039(00)78730-2

  日期：1980.1

  The concerted mechanism for the stannic chloride catalysed cyclisation of aryl cyclopropyl ketones is disproved by trapping the intermediate. The reaction provides a facile route to γ-hydroxyketones.

  捕集中间体无法证明氯化锡催化芳基环丙基酮的环化反应。该反应提供了容易的途径来制备γ-羟基酮。
• Total synthesis of (±)-picropodophyllone
  作者：William S. Murphy、Sompong Wattanasin

  DOI：10.1039/p19820000271

  日期：——

  Following model studies, the synthesis of (±)-picropodophyllone was completed by first cyclopropanating the appropriate chalcone (11) with ethoxycarbonyl dimethylsulphonium methylide. Treatment of the resulting cyclopropyl ketone with stannic chloride in either benzene or methylene chloride failed but in nitromethane the tetralone (1Oa) was formed. The lactose ring was completed using formaldehyde

  根据模型研究，首先通过将合适的查尔酮（11）与乙氧基羰基二甲基甲磺酸甲酯环丙烷化，完成（±）-鬼臼苦素的合成。用氯化锡在苯或二氯甲烷中处理所得的环丙基酮失败，但在硝基甲烷中形成四氢萘酮（10a）。使用甲醛完成乳糖环，基于查尔酮的总产率为40％。
• Intermediates for the production of epipodophyllotoxin and related
  申请人：Bristol-Myers Company

  公开号：US04644072A1

  公开（公告）日：1987-02-17

  There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.

  提供了一种新颖而高效的立体选择性全合成epipodophyllotoxin及相关的epipodophyllotoxin化合物，其一般式为##STR1##其中，R.sup.1和R.sup.2各自独立地为氢或(较低的)烷氧基，或者R.sup.1和R.sup.2一起为亚甲二氧基；R.sup.4和R.sup.6各自独立地为氢或(较低的)烷氧基；R.sup.5为氢或苯酚保护基；或其酸加成盐。本发明还提供了新的中间体和制备这些中间体的工艺，然后将它们转化为已知的抗肿瘤药物。
• Intermediates for the production of epipodophylotoxin and related
  申请人：Bristol-Myers Company

  公开号：US04728740A1

  公开（公告）日：1988-03-01

  There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.

  本发明提供了一种新颖和高效的立体选择性全合成环柿木毒素及相关环柿木毒素化合物，其一般式为##STR1##其中R.sup.1和R.sup.2各自独立地为氢或(较低)烷氧基，或R.sup.1和R.sup.2一起为亚甲二氧基；R.sup.4和R.sup.6各自独立地为氢或(较低)烷氧基；R.sup.5为氢或苯酚保护基；或其酸盐加合物。本发明还提供了新的中间体和制备该中间体的过程，然后将其转化为已知的抗肿瘤药物。
• Murphy, William S.; Wattanasin, Sompong, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1445 - 1452
  作者：Murphy, William S.、Wattanasin, Sompong

  DOI：——

  日期：——