(rac)-trans-octahydro-2H-indol-2-one | 1195-13-7

• 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: (rac)-trans-octahydro-2H-indol-2-one
• 英文别名: trans-7-azabicyclo<4.3.0>nonan-8-one；trans-Hexahydro-oxindol；(+/-)-trans-octahydro-indol-2-one；(+/-)-trans-Octahydro-indol-2-on；(3AR,7AS)-Octahydro-2H-indol-2-one；(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydroindol-2-one
• CAS: 1195-13-7；56921-07-4；90154-87-3；131348-77-1；131348-78-2；143679-79-2
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: GFOOVKOSROWXAZ-RQJHMYQMSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  122-124 °C(Press: 5 Torr)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (rac)-trans-octahydro-2H-indol-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以32%的产率得到trans-2-aminocyclohexylacetic acid
  参考文献：
  名称：

  受限构象的γ-氨基丁酸类似物的合成。第1部分。2-氨基环烷基乙酸

  摘要：

  描述了作为受限构象的γ-氨基丁酸类似物的顺式和反式-2-氨基环丙基，-环丁基，-环戊基和-环己基乙酸的合成。质谱证据完全支持构型异构体的立体化学分配。

  DOI：

  10.1039/p19820002553
• 作为产物：
  描述：

  trans-2-(prop-2-enyl)cyclohexylamine 在 盐酸 、 potassium permanganate 、 溶剂黄146 、 丙酮 作用下， 生成 (rac)-trans-octahydro-2H-indol-2-one
  参考文献：
  名称：

  550.还原环状碱基的合成和立体化学研究。第六部分 反式八氢吲哚的新合成及其霍夫曼甲基化产物的重新研究

  摘要：

  DOI：

  10.1039/jr9580002688

文献信息

• Iridium-Catalyzed Enantioselective C(sp³)–H Amidation Controlled by Attractive Noncovalent Interactions
  作者：Hao Wang、Yoonsu Park、Ziqian Bai、Sukbok Chang、Gang He、Gong Chen

  DOI：10.1021/jacs.9b02811

  日期：2019.5.1

  enantioselective C(sp3)-H functionalization reactions are still highly desirable. In particular, the ability to use attractive noncovalent interactions for rate acceleration and enantiocontrol would significantly expand the current arsenal for asymmetric metal catalysis. Herein, we report the development of a highly enantioselective Ir(III)-catalyzed intramolecular C(sp3)-H amidation reaction of dioxazolone

  尽管在过去十年中取得了显着进展，但在对映选择性 C(sp3)-H 官能化反应中手性催化剂的新设计策略仍然是非常需要的。特别是，使用有吸引力的非共价相互作用进行速率加速和对映控制的能力将显着扩展不对称金属催化的当前武器库。在此，我们报告了高对映选择性 Ir(III) 催化的二恶唑酮底物的分子内 C(sp3)-H 酰胺化反应的开发，该反应用于使用新设计的基于 α-氨基酸的手性配体合成光学富集的 γ-内酰胺。这种 Ir 催化的反应在非常温和的条件下以优异的效率进行，并对活化和未活化的烷基 C(sp3)-H 键具有出色的对映选择性。它为γ-烷基γ-内酰胺的不对称合成提供了第一条通用路线。发现水是一种独特的共溶剂，可在 γ-芳基内酰胺生产中实现出色的对映选择性。机理研究表明，配体在 Ir 中心周围形成了一个明确的凹槽型手性袋。该口袋的疏水作用允许在极性或水性介质中轻松立体控制底物结合。这种新的 Ir
• [EN] A METHOD FOR THE PREPARATION OF (2S, 3AR, 7AS)-OCTAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID AS KEY INTERMEDIATE IN THE PREPARATION OF TRANDOLAPRIL BY REACTING A CYCLOHEXYL AZIRIDINE WITH A DIALKYL MALONATE<br/>[FR] PROCEDE DE PREPARATION DE (2S, 3AR, 7AS)-OCTAHYDRO-1H-INDOLE-2-ACIDE CARBOXYLIQUE EN TANT QU'INTERMEDIAIRE DANS LA PREPARATION DE TRANDOLAPRIL PAR REACTION D'UN CYCLOHEXYL AZIRIDINE AVEC UN DIALKYL MALONATE
  申请人：TEXCONTOR ETS

  公开号：WO2005054194A1

  公开（公告）日：2005-06-16

  A method for the synthesis of a compound of formula (I) as a mixture of enantiomers, formula (I) (wherein R1 is H or an acid protective group and H+A- indicates an optional acid with which the compound of formula (I) may form an ammonium salt) said method comprising; A) reacting a cyclohexyl aziridine with a dialkyl malonate, whereby to provide a trans-fused 3-alkylcarbonyl-octahydro-indol-2-one; B) decarbonylation at the 3-position, conversion of the ketone of the resulting trans-octahydro-indol-2-one to an optionally protected carboxylic acid group; and C) optionally removing any N-substitution if necessary.

  一种合成式(I)化合物的方法，该化合物为对映体的混合物，式(I)如下（其中R1为H或酸保护基，H+A-表示化合物(I)可能形成铵盐的可选酸）该方法包括：A）将环己基环氧丙烷与二烷基丙二酸酯反应，从而提供顺式螺环3-烷基羰基-八氢吲哚-2-酮；B）在3位脱羰基，将所得的顺式八氢吲哚-2-酮的酮基转化为可选的保护羧酸基；以及C）如有必要，可选择性地去除任何N取代基。
• Method for the Preparation of (2S, 3AR, 7AS)-Octahydro-III-Indole-2-Carboxylic Acid as Key Intermediate in the Preparation of Trandolapril by Reacting a Cyclohexyl Aziridine with a Dialkyl Malonate
  申请人：Cid Pau

  公开号：US20070225505A1

  公开（公告）日：2007-09-27

  A method for the synthesis of a compound of formula I as a mixture of enantiomers, (wherein R 1 is H or an acid protective group and H + A − indicates an optional acid with which the compound of formula I may form an ammonium salt) said method comprising; A) reacting a cyclohexyl aziridine with a dialkyl malonate, whereby to provide a trans-fused 3-alkylcarbonyl-octahydro-indol-2-one; B) decarbonylation at the 3-position, conversion of the ketone of the resulting trans-octahydro-indol-2-one to an optionally protected carboxylic acid group; and C) optionally removing any N-substitution if necessary.

  一种合成式I化合物的方法，该化合物为对映体混合物，其中R1为H或酸保护基，H+A−表示该化合物可以形成铵盐的可选酸。该方法包括：A）将环己基氮杂环与二烷基丙二酸酯反应，从而提供反式螺环3-烷基酰基-八氢吲哚-2-酮；B）在3位脱羰基化，将所得反式八氢吲哚-2-酮的酮转化为可选的保护羧酸基；C）必要时可选择性地去除任何N-取代基。
• Analogs of Ac-CCK-7 incorporating dipeptide mimics in place of Met28-Gly29
  作者：Jefferson W. Tilley、Waleed Danho、Shian Jan Shiuey、Irina Kulesha、Joseph Swistok、Raymond Makofske、Joseph Michalewsky、Joseph Triscari、David Nelson

  DOI：10.1021/jm00099a005

  日期：1992.10

  A series of analogs of Ac-CCK-7 [Ac-Tyr(SO3H)-Met28-Gly29-Trp-Met-Asp-Phe-NH2, (1)] Were prepared in which the Met28-Gly29 dipeptide was replaced by omega-aminoalkanoic acids. Compounds were assessed in binding assays using homogenated rat pancreatic membranes and bovine striatum as the source of CCK-A and CCK-B receptors, respectively, and for anorectic activity after intraperitoneal administration to rats. The analog incorporating 4-aminobutanoic acid (5) was only 8 times less potent than 1 in the pancreatic binding assay, was more potent in the striatal binding assay, and was more potent than 1 in reducing food intake in rats. Using a bioactive cyclic analog of Ac-CCK-7 as a template, several rigid spacers were designed and tested as substitutes for the Met28-Gly29 dipeptide. The analogs incorporating 3-aminobenzoic acid (20) and (1S)-trans-2-aminocyclopentanecarboxylic acid (26) proved highly effective in the binding assays and as anorectic agents. We hypothesize that for stimulation of CCK-A receptors, the main function of the N-terminal tripeptide of Ac-CCK-7 is to orient the tyrosine sulfate with respect to Trp30 and that the bioactive arrangement of these elements lies among those which are readily available to both 20 and 26. NOESY and distance-constrained molecular dynamics experiments carried out on 20 and 26 identified conformations in which the relative orientation of the tyrosine hydroxide and the alpha-carbon atom of tryptophan were similar, providing the basis for further drug design efforts.
• A METHOD FOR THE PREPARATION OF (2S, 3AR, 7AS)-OCTAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID AS KEY INTERMEDIATE IN THE PREPARATION OF TRANDOLAPRIL BY REACTING A CYCLOHEXYL AZIRIDINE WITH A DIALKYL MALONATE
  申请人：Texcontor Etablissement

  公开号：EP1687271A1

  公开（公告）日：2006-08-09