cis-octahydro-1-methylindol-2-one

• 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: cis-octahydro-1-methylindol-2-one
• 英文别名: (3aS,7aS)-1-methyl-3a,4,5,6,7,7a-hexahydro-3H-indol-2-one
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: PYQWQYZNDDQKNY-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-cyclohexylidenemethylamine 在 sodium periodate 、 镍 、 三氟乙酸酐 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 cis-octahydro-1-methylindol-2-one
  参考文献：
  名称：

  Acid-catalyzed cyclizations of n-vinyl-α-sulfinylacetamides A novel synthetic approach to erythrinane

  摘要：

  DOI：

  10.1016/s0040-4039(00)87302-5

文献信息

• Diastereoselective Rhodium-Catalyzed Hydrogenation of 2-Oxindoles and 3,4-Dihydroquinolones
  作者：Christian H. Schiwek、Christian Jandl、Thorsten Bach

  DOI：10.1021/acs.orglett.0c03427

  日期：2020.12.18

  The benzene ring of indolin-2-ones (2-oxindoles) and 3,4-dihydroquinol-2-ones was converted to a saturated cyclohexane ring by hydrogenation in the presence of the rhodium complex Cy(CAAC)Rh(cod)Cl. The stereoselectivity of the process was found to be high with respect to both external substituent R1 within the saturated part of the heterocyclic ring and substituent X on the benzene ring. Twenty-one

  在铑配合物Cy（CAAC）Rh（cod）Cl的存在下，通过氢化将吲哚-2-酮（2-氧吲哚）和3,4-二氢喹啉-2-酮的苯环转化为饱和的环己烷环。发现该方法相对于杂环的饱和部分内的外部取代基R 1和苯环上的取代基X均具有较高的立体选择性。21个六氢吲哚-2（3 H）-一（产率70-99％，dr = 83/17至> 99/1）和十二个八氢-2（1 H）-喹啉酮（87-96％产率，dr =得到64/36至> 99/1）的主要非对映异构体，其氢原子呈顺式安排。对官能团的高耐受性以及与现有立体异构中心的相容性是此处介绍的氢化方案的关键特征。
• Synthesis of γ-lactams via Ru(II)–Pheox-catalyzed regioselective intramolecular Csp3–H insertion of diazoacetamides
  作者：Takuji Fujii、Huong Dang Thi Thu、Seiji Iwasa

  DOI：10.1016/j.tetlet.2020.152276

  日期：2020.9

  Herein, γ-lactam derivatives are obtained in high yield via highly regioselective intramolecular Csp3–H insertion reactions of α-diazoacetamides catalyzed by a rac-Ru(II)–Pheox complex. The catalytic system is applicable to a wide range of diazoacetamides under mild conditions to produce the corresponding γ-lactams.

  在此，以高收率得到γ-内酰胺衍生物通过高度选择性分子内CSP 3通过催化α-diazoacetamides的-H插入反应外消旋-Ru（II）-Pheox复杂。该催化体系可在温和条件下应用于各种重氮乙酰胺，以生产相应的γ-内酰胺。
• Novel synthesis of pyrrolidinones by cobalt carbonyl catalyzed carbonylation of azetidines. A new ring-expansion-carbonylation reaction of 2-vinylazetidines to tetrahydroazepinones
  作者：Dominique Roberto、Howard Alper

  DOI：10.1021/ja00201a040

  日期：1989.9

  Pyrrolidinones can be synthesized in high yields and regioselectivity by the cobalt carbonyl catalyzed carbonylation of azetidines. For 2-substituted azetidines (alkyl, aryl, CH 2 OH, CH 2 OR, CH 2 OCOR, and COOR), carbonyl insertion occurs in the more or less substituted ring carbon-nitrogen bond depending on the kind of substituent group and on the reaction temperature. In the case of 2-vinylazetidines

  吡咯烷酮可以通过羰基钴催化的氮杂环丁烷羰基化以高产率和区域选择性合成。对于 2-取代的氮杂环丁烷（烷基、芳基、CH 2 OH、CH 2 OR、CH 2 OCOR 和 COOR），羰基插入发生在或多或少取代的环碳 - 氮键中，这取决于取代基的种类和反应温度。在 2-乙烯基氮杂环丁烷的情况下，扩环和羰基化得到七元环四氢氮杂环酮。在这些反应中观察到良好的官能团耐受性
• Synthesis of (±)-mesembranol by radical cyclisation of α,α-dichloroacetamides
  作者：Hiroyuki Ishibashi、Taru Su So、Tatsunori Sato、Katsuko Kuroda、Masazumi Ikeda

  DOI：10.1039/c39890000762

  日期：——

  (±)-Mesembranol was synthesised in a highly stereoselective manner using Bu3SnH mediated radical cyclisation of α,α-dichloroacetamide as the key step.

  以Bu 3 SnH介导的α，α-二氯乙酰胺自由基环化为关键步骤，以高度立体选择性的方式合成了（±）-Mesembranol 。
• Radical cyclization of N-(cyclohex-2-enyl)-.alpha.,.alpha.-dichloroacetamides. Stereoselective syntheses of (.+-.)-mesembranol and (.+-.)-elwesine
  作者：Hiroyuki Ishibashi、Taru Su So、Kyoko Okochi、Tatsunori Sato、Nobuyuki Nakamura、Hiroshi Nakatani、Masazumi Ikeda

  DOI：10.1021/jo00001a021

  日期：1991.1

  Stereoselective syntheses of the Sceletium alkaloid (+/-)-mesembranol (2) and the Amaryllidaceae alkaloid (+/-)-elwesine (3) have been achieved. A key step in the syntheses involves the Bu3SnH-mediated radical cyclization of the dichloroacetamides 34 and 46, which provides the cis-3a-aryloctahydroindolones 36 and 47, respectively. The amides 34 and 46 were prepared in a highly stereocontrolled manner from the corresponding 1-arylcyclohexenes 29 and 41 along the lines: 29 --> 30a --> 31 --> 32 --> 33 --> 34 and 41 --> 42a --> 44a --> 45a --> 46. Transformation of 36 into (+/-)-mesembranol was readily accomplished by reduction with diborane and subsequent removal of the O-benzyl protecting group by hydrogenolysis over Pd/C. On the other hand, debenzylation of 36 with Raney Ni afforded a mixture of the 6-alpha- and 6-beta-alcohols 39a and 39b, which was then reduced by alane to give a separable mixture of (+/-)-mesembranol and (+/-)-6-epimesembranol (40). Reduction of 47 with diborane followed by catalytic hydrogenolysis over Pd/C afforded the amino alcohol 50, which has already been converted into (+/-)-elwesine by Pictet-Spengler cyclization.