3-[(1R,5R,8R)-8-iodo-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]propanal | 85585-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-[(1R,5R,8R)-8-iodo-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]propanal
• CAS: 85585-60-0
• 化学式: C₁₀H₁₁IO₃
• 分子量: 306.1
• InChiKey: USDQBCWOCSDITO-KHQFGBGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[(1R,5R,8R)-8-iodo-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]propanal 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 苯 为溶剂， 生成 rel-(1S,3aS,7R,7aS)-Ethyl 1,2,3,6,7,7a-hexahydro-α(S)-methyl-9-oxo-7,3a-(epoxymethano)-3aH-indene-1-acetate
  参考文献：
  名称：

  通过立体选择性自由基环化制备胸膜素和岩gen碱的cde-ring系统

  摘要：

  描述了内酯3的合成，内酯3是通向胸膜素（1）和地精子（2）的一种预计中间体。使用立体选择性自由基环化（5→9）构建反式-全氢茚满核。

  DOI：

  10.1016/s0040-4039(00)89241-2
• 作为产物：
  描述：

  (1R,5R,8R)-1-[2-(1,3-dioxolan-2-yl)ethyl]-8-iodo-6-oxabicyclo[3.2.1]oct-2-en-7-one 以91%的产率得到
  参考文献：
  名称：

  CHUANG, CHE-PING;GALLUCCI, JUDITH C.;HART, DAVID J., J. ORG. CHEM., 53,(1988) N 14, C. 3210-3218

  摘要：

  DOI：

文献信息

• Free-radical cyclizations: application to the total synthesis of dl-pleurotin and dl-dihydropleurotin acid
  作者：David J. Hart、Horng Chih Huang、Ram Krishnamurthy、Theresa Schwartz

  DOI：10.1021/ja00201a035

  日期：1989.9

  antitumor antibiotic pleurotin (1) and dihydropleurotin acid (2) are described. Early stages of the synthesis feature the construction of a trans perhydroindan substructure using a stereoselective free-radical cyclization, and the final stage of the synthesis involves the biomimetic conversion of dihydropleurotin acid (2) to pleurotin (1)

  描述了抗肿瘤抗生素 pleurotin (1) 和 dihydropleurotin acid (2) 的全合成。合成的早期阶段特征是使用立体选择性自由基环化构建反式全氢茚满亚结构，合成的最后阶段涉及二氢侧切花酸 (2) 到侧切叶酸 (1) 的仿生转化
• A new entry to highly functionalized perhydroindans via free radical cyclizations
  作者：Che Ping Chuang、David J. Hart

  DOI：10.1021/jo00158a045

  日期：1983.5
• Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates
  作者：David J. Hart、Ramanarayanan Krishnamurthy

  DOI：10.1021/jo00042a029

  日期：1992.7

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.
• Preparation of functionalized trans-perhydroindans from substituted benzoic acids: reductive alkylation-halolactonization-free radical cyclization
  作者：Che Ping Chuang、Judith C. Gallucci、David J. Hart

  DOI：10.1021/jo00249a014

  日期：1988.7
• HART, DAVID J.;HUANG, HORNG-CHIH;KRISHNAMURTHY, RAM;SCHWARTZ, THERESA, J. AMER. CHEM. SOC., 111,(1989) N9, C. 7507-7519
  作者：HART, DAVID J.、HUANG, HORNG-CHIH、KRISHNAMURTHY, RAM、SCHWARTZ, THERESA

  DOI：——

  日期：——