1,3-bis(ethylenedioxy)-2-(1-iodopropyl)-2-methylcyclohexane | 474956-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-bis(ethylenedioxy)-2-(1-iodopropyl)-2-methylcyclohexane
• 英文别名: 6-methyl-6-(3-iodopropyl)-1,4,8,11-tetraoxadispiro[4.1.4.3]tetradecane；6-(3-Iodopropyl)-6-methyl-1,4,8,11-tetraoxadispiro[4.1.47.35]tetradecane
• CAS: 474956-29-1
• 化学式: C₁₄H₂₃IO₄
• 分子量: 382.239
• InChiKey: DZNFPICHKSYHRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(ethylenedioxy)-2-(1-iodopropyl)-2-methylcyclohexane 在 高氯酸 、 diethylzinc 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 (1S,8aS)-5-Hydroxymethyl-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol
  参考文献：
  名称：

  Asymmetric construction of novel bicyclo[4.4.0] and [4.3.0]ring systems via intramolecular Horner–Wadsworth–Emmons reactions

  摘要：

  Novel perhydro-indanones and -naphthalenones having a quaternary stereogenic carbon and tetrasubstituted olefinic linkage were prepared via asymmetric intramolecular Horner-Wadsworth-Emmons reactions. The optically active binaphthyl phosphonates were connected with the 2-substituted cyclopenta- or cyclohexa-1,3-dione through the linker arm and the successive base treatment of the products with diethylzinc led to cyclization reactions with concomitant differentiation of diastereotopic carbonyl groups to afford the non-racemic title compounds in good enantiomeric excess. The absolute structure of the cyclized product was determined by X-ray analysis of its derived bromide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00177-5
• 作为产物：
  描述：

  2-allyl-3-ethylenedioxy-2-methylcyclohexanone 在 dimethyl sulfide borane 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 30.5h， 生成 1,3-bis(ethylenedioxy)-2-(1-iodopropyl)-2-methylcyclohexane
  参考文献：
  名称：

  Asymmetric construction of novel bicyclo[4.4.0] and [4.3.0]ring systems via intramolecular Horner–Wadsworth–Emmons reactions

  摘要：

  Novel perhydro-indanones and -naphthalenones having a quaternary stereogenic carbon and tetrasubstituted olefinic linkage were prepared via asymmetric intramolecular Horner-Wadsworth-Emmons reactions. The optically active binaphthyl phosphonates were connected with the 2-substituted cyclopenta- or cyclohexa-1,3-dione through the linker arm and the successive base treatment of the products with diethylzinc led to cyclization reactions with concomitant differentiation of diastereotopic carbonyl groups to afford the non-racemic title compounds in good enantiomeric excess. The absolute structure of the cyclized product was determined by X-ray analysis of its derived bromide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00177-5

文献信息

• Synthesis of Racemic and Enantiomerically Pure Acetylenic ω-Keto Esters Derived from 2-Methyl-1,3-cycloalkanediones and 2-Methylcycloalkanones Respectively
  作者：Michel Miesch、Philippe Geoffroy、Marie-Paule Ballet、Sidonie Finck、Eric Marchioni、Christophe Marcic

  DOI：10.1055/s-0029-1217043

  日期：2010.1

  Racemic and enantiomerically pure alkynyl esters tethered, respectively, to 2-methyl-1,3-cycloalkanediones and 2-methyl­cycloalkanones were readily obtained starting from common intermediates, which were available on large scale. alkynyl ester - enantiomer-chain - elongation - trimethylsilylpropyne - Corey-Fuchs reaction

  从常见的中间体开始容易地获得分别连接到2-甲基-1,3-环烷二酮和2-甲基环烷酮的外消旋和对映体纯的炔基酯，这些中间体可以大规模获得。 炔基酯-对映体链-伸长率-三甲基甲硅烷基丙炔-Corey-Fuchs反应