(1S*,2R*,6S*,7R*)-10-cyclohexylidene-4-oxa-tricyclo[5.2.1.02.6]-dec-8-ene-3,5-dione | 67968-60-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S*,2R*,6S*,7R*)-10-cyclohexylidene-4-oxa-tricyclo[5.2.1.02.6]-dec-8-ene-3,5-dione
• 英文别名: 7-cyclohexyLiDene-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride；7-Cyclohexyliden-norborn-5-en-2endo,3endo-dicarbonsaeure-anhydrid；7-Cyclohexylidennorbornen-5,6-dicarbonsaeureanhydrid；(1R,2S,6R,7S)-10-cyclohexylidene-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 67968-60-9
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: KHUIRUIZWPEMNL-NIFPGPBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S*,2R*,6S*,7R*)-10-cyclohexylidene-4-oxa-tricyclo[5.2.1.02.6]-dec-8-ene-3,5-dione 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(1S*,2R*,3S*,4R*)-7-cyclohexylidene-2,3-di(hydroxymethyl)bicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Synthesis of cis,cis,cis-1-alkylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentanes

  摘要：

  A new strategy to prepare tetradentate or pentadentate diphenylphosphine ligands has been explored from Diels-Alder adducts of fulvenes and maleic anhydride. A tetradentate phosphine ligand, bearing a side chain allowing the formation of a bond with polystyrene resin, has been prepared in seven steps from cyclopentadiene. The cis,cis,cis-1-cyclohexylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentane (Cyclo-Tedicyp) in combination with [PdCl(C3H5)](2) led to an efficient catalyst for the Heck, Suzuki and Sonogashira coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.016
• 作为产物：
  描述：

  马来酸酐 、 cyclopenta-2,4-dien-1-ylidenecyclohexane 在 乙醚 作用下， 生成 (1S*,2R*,6S*,7R*)-10-cyclohexylidene-4-oxa-tricyclo[5.2.1.02.6]-dec-8-ene-3,5-dione
  参考文献：
  名称：

  Alder; Ruehmann, Justus Liebigs Annalen der Chemie, 1950, vol. 566, p. 1,19

  摘要：

  DOI：

文献信息

• The Diels—Alder Reaction in the Fulvene Series
  作者：E. P. Kohler、John Kable

  DOI：10.1021/ja01308a042

  日期：1935.5
• Unprecedented Microwave Effects on the Cycloaddition of Fulvenes. A New Approach to the Construction of Polycyclic Ring Systems
  作者：Bor-Cherng Hong、Yeong-Jou Shr、Ju-Hsiou Liao

  DOI：10.1021/ol017304q

  日期：2002.2.1

  [GRAPHICS]Novel cycloaddition reactions between fulvenes and various alkenes and alkynes are promoted by the use of microwave irradiation. These processes result in the formation of intriguing polycyclic ring systems such as those found in isobarbatene, alcyopterosin, and enokipodin A. Importantly, these reactions do not occur under conventional thermolytic conditions.
• Studies on Diene-addition Reactions. II.¹ The Reaction of 6,6-Pentamethylenefulvene with Maleic Anhydride
  作者：R. B. Woodward、Harold Baer

  DOI：10.1021/ja01232a042

  日期：1944.4
• Reactions of molecular crystals with gases. III. Relation of anisotropy to crystal structure in reactions of carboxylic acids and anhydrides with ammonia gas
  作者：Rodger S. Miller、David Y. Curtin、Iain C. Paul

  DOI：10.1021/ja00827a016

  日期：1974.10