(2R^*,3R^*)-2-allyl-3-<(1R^*)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone | 88099-38-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R^*,3R^*)-2-allyl-3-<(1R^*)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone
• 英文别名: (2R^*,3R^*)-2-allyl-3-[(1R^*)-2-(methoxycarbonyl)-1-methylethyl]-2-methylcyclopentanone；methyl (3S)-3-[(1S,2S)-2-methyl-3-oxo-2-prop-2-enylcyclopentyl]butanoate
• CAS: 88099-38-1；131432-96-7；146502-04-7
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: UHUOIUTZDBNKSB-MJVIPROJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R^*,3R^*)-2-allyl-3-<(1R^*)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone 在 Pd-BaSO₄ 、 钯 sodium hydroxide 、 lithium aluminium tetrahydride 、 jones' reagent 、 sodium hydroperoxide 、 Celite 、 氢气 、 sodium acetate 、 二(3-甲基丁烷-2-基)硼烷 、 乙酸酐 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 de-AB-cholestan-9-one
  参考文献：
  名称：

  Application of dithianylidene anions to the synthesis of de-ab-8-carbomethoxycholestan-9-one: a steroid and vitamin D synthon

  摘要：

  DOI：

  10.1016/s0040-4039(00)81790-6
• 作为产物：
  描述：

  甲基环戊烯醇酮 在 mercury dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 (2R^*,3R^*)-2-allyl-3-<(1R^*)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone
  参考文献：
  名称：

  Application of dithianylidene anions to the synthesis of de-ab-8-carbomethoxycholestan-9-one: a steroid and vitamin D synthon

  摘要：

  DOI：

  10.1016/s0040-4039(00)81790-6

文献信息

• Chemoenzymatic preparation of functionalized bicyclo[3.2.1]octenone and practical utilization
  作者：Shinichiro Ito、Ayako Tosaka、Keisuke Hanada、Masatoshi Shibuya、Kunio Ogasawara、Yoshiharu Iwabuchi

  DOI：10.1016/j.tetasy.2007.12.009

  日期：2008.2

  the synthesis of both enantiomers of a functionalized bicyclo[3.2.1]octenone, which is potentially useful as a versatile chiral building block, has been developed from 1,4-cyclohexanedione monoethylene acetal by employing proline-catalyzed diastereoselective intramolecular aldolization and lipase-mediated kinetic resolution as the key steps. The synthetic utility of the bicyclo[3.2.1]octenone has been

  通过使用脯氨酸催化的非对映选择性分子内缩醛反应，从1,4-环己烷二酮单乙缩醛开发了一种实用的合成功能化双环[3.2.1]辛烯酮的对映异构体的方法，该化合物可能用作通用的手性构建基。和脂肪酶介导的动力学拆分是关键步骤。通过转化为手性双环[5.3.0]癸烷，已证明了双环[3.2.1]辛烯酮的合成效用，该手性应用作合成抗肿瘤倍半萜假拟番石榴酸内酯类的关键中间体。
• Synthesis of vitamin D3 D ring synthons by reductive cleavage of norbornan-6-one-2-carboxylates
  作者：Isao Shimizu、Naoto Matsuda、Yasuo Noguchi、Yoshiro Zako、Kazuo Nagasawa

  DOI：10.1016/s0040-4039(00)97763-3

  日期：1990.1

  Reductive cleavage of 5-methylnorbornan-6-one-2-carboxylates with lithium metal in liquid ammonia gave 3-(1-methyl-2-methoxycarbonylethyl)cyclopentanones in good yields.

  在液态氨中用锂金属对5-甲基降冰片烷-6-一-2-羧酸酯进行的还原裂解，得到了3-（1-甲基-2-甲氧基羰基乙基）环戊烷，收率很高。
• Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring
  作者：Kazuo Nagasawa、Naoto Matsuda、Yasuo Noguchi、Masahiro Yamanashi、Yoshiro Zako、Isao Shimizu

  DOI：10.1021/jo00058a032

  日期：1993.3

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.