(2-exo)-methylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid | 32190-81-1

• 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: (2-exo)-methylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid
• 英文别名: exo-2-Methyl-endo-2-carboxybicyclo<2.2.1>hept-5-ene；2-exo-methyl-5-norbornene-2-endo-carboxylic acid；(+/-)-2-methyl-norborn-5-ene-2endo-carboxylic acid；(+/-)-2-Methyl-norborn-5-en-2endo-carbonsaeure；(+/-)-2exo-Methyl-norbornen-(5)-carbonsaeure-(2endo)；exo-2-methyl-bicyclo(2.2.1)hept-5-en-endo-2-carboxylic acid；Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1S-endo)-(9CI)；(1S,2S,4S)-2-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS: 32190-81-1
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: JIHFJSOMLKXSSQ-OOZYFLPDSA-N

物化性质

• 沸点：
  261.4±19.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-exo)-methylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid 在 氯化亚砜 作用下， 反应 5.0h， 生成 (+-)-2-methyl-norborn-5-ene-2endo-carbonyl chloride
  参考文献：
  名称：

  Intramolecular carbene chemistry. Evidence for exclusive C-H insertion in 8-methylene-2-noradamantylidene

  摘要：

  DOI：

  10.1021/jo00256a028
• 作为产物：
  描述：

  5-norbornene-2-carbonitrile 在 氢氧化钾 、 sodium amide 作用下， 生成 (2-exo)-methylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid
  参考文献：
  名称：

  Stereochemistry of Diels-Alder Adducts. II. The Alkylation of Some Bicyclic Nitriles

  摘要：

  DOI：

  10.1021/ja01553a044

文献信息

• Bicyclische Verbindungen—X ringerweiterung von norbornanderivaten—III
  作者：W. Kraus、P. Schmutte

  DOI：10.1016/s0040-4020(01)82460-1

  日期：1968.1

  The deamination of endo- and exo-2-methyl-2-aminomethyl-norbornane with nitrous acid and the hydrolysis of endo- and exo-2-methyl-2-tosyloxymethyl-norbornane has been investigated by gas-chromatography. The ratio of tertiary methyl-bicyclo[3.2.1.]octanols-3 and -2 formed by carbon shift involving the C-1, C-2 bond and the C-2, C-3 bond, respectively, is chiefly controlled by steric factors. From the

  的脱氨基内切-和外切-2-甲基-2-氨基甲基降冰片烷与亚硝酸和的水解内切-和外切-2-甲基-2-甲苯磺酰氧基甲基降冰片烷已经通过气相色谱分析。分别通过涉及C-1，C-2键和C-2，C-3键的碳转移形成的叔甲基-双环[3.2.1。]辛醇-3和-2的比率主要受以下因素控制：空间因素。从产品组成可以得出结论，非经典的双环辛基阳离子不参与环的扩展反应。
• Zirconocene-catalyzed cationic Diels-Alder reactions
  作者：Peter Wipf、Wenjing Xu

  DOI：10.1016/0040-4020(94)01140-u

  日期：1995.4

  In situ prepared Cp2ZrCl⊕ catalyzes the formation of dioxolenium ions from α,β-unsaturated epoxy esters. As a consequence of this activation process, acrylate, methacrylate and crotonate derivatives undergo a rapid and stereoselective cationic [4+2] cycloaddition with a wide range of dienes. Ring-extended carboxylic acid derivatives are formed in 1–7 h at 0–21 °C and in 50–90% yield after saponification

  原位制备的Cp 2的ZrCl ⊕催化从α，β不饱和环氧酯dioxolenium离子的形成。作为该活化过程的结果，丙烯酸酯，甲基丙烯酸酯和巴豆酸酯衍生物经历了具有广泛二烯的快速且立体选择性的阳离子[4 + 2]环加成。中间体二醇酯皂化后，在0–21°C下于1–7 h内形成扩环的羧酸衍生物，产率为50–90％。通过简单的Cp路易斯酸催化2的ZrCl ⊕可以被排除的实验结果的基础上。
• Highly diastereoselective Diels-Alder reaction of optically active ethyl 2-p-tolylsulfinylmethylenepropionate with cyclopentadiene
  作者：Toru Koizumi、Ichiro Hakamada、Eiichi Yoshii

  DOI：10.1016/s0040-4039(01)91155-4

  日期：1984.1

  Stereochemistry of the Diels-Alder reaction of ethyl Z- and E-2-ptolylsulfinylmethylenepropionate with cyclopentadiene has been studied. The high diastereoselectivity was observed especially in the case of exo-cycloaddition.

  研究了Z-乙基和E-2-戊基亚磺酰基亚甲基丙酸乙酯与环戊二烯的Diels-Alder反应的立体化学。特别是在外环加成的情况下，观察到高非对映选择性。
• [EN] BICYCLIC INDOLYL DERIVATIVES AND METHODS OF THEIR USE AS SEROTONERGIC AGENTS<br/>[FR] DERIVES D'INDOLYLE BICYCLIQUES, ET PROCEDES RELATIFS A LEUR UTILISATION COMME AGENTS SEROTONERGIQUES
  申请人：WYETH CORP

  公开号：WO2004111035A1

  公开（公告）日：2004-12-23

  Bicyclic indolyl derivatives and compositions containing such compounds are disclosed. Methods of using the bicyclic indolyl derivatives and compositions containing such composition as serotonergic agents, such as in the treatment of depression and anxiety, are also disclosed. In addition, processes for the preparation of bicyclic indolyl derivatives are disclosed.

  本文披露了双环吲哚衍生物及含有这种化合物的组合物。还披露了使用双环吲哚衍生物和含有这种组合物作为5-羟色胺能药物的方法，例如用于治疗抑郁症和焦虑症。此外，还披露了制备双环吲哚衍生物的过程。
• Bartlett et al., Justus Liebigs Annalen der Chemie, 1959, vol. 623, p. 217,247
  作者：Bartlett et al.

  DOI：——

  日期：——