(9H-fluoren-9-yl)methyl (2E,4E)-5-iodopenta-2,4-dienylcarbamate | 955959-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (2E,4E)-5-iodopenta-2,4-dienylcarbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2E,4E)-5-iodopenta-2,4-dienyl]carbamate
• CAS: 955959-50-9
• 化学式: C₂₀H₁₈INO₂
• 分子量: 431.273
• InChiKey: LFSRLMCBXBIJBH-VIKAGGQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (2E,4E)-5-iodopenta-2,4-dienylcarbamate 在 吡啶 、 chromium dichloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 40.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Oxazolomycin A

  摘要：

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

  DOI：

  10.1021/ol202306d
• 作为产物：
  描述：

  (9H-芴-9-基)甲基 烯丙基氨基甲酸酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 chromium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 69.0h， 生成 (9H-fluoren-9-yl)methyl (2E,4E)-5-iodopenta-2,4-dienylcarbamate 、 (9H-fluoren-9-yl)methyl (2E,4Z)-5-iodopenta-2,4-dienylcarbamate
  参考文献：
  名称：

  Total Synthesis of Oxazolomycin A

  摘要：

  The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene gamma-lactam/beta-lactone antibiotic, is described. Key features Include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

  DOI：

  10.1021/ol202306d

文献信息

• Asymmetric Synthesis of the Fully Elaborated Pyrrolidinone Core of Oxazolomycin A
  作者：Timothy J. Donohoe、Timothy J. C. O’Riordan、Manuel Peifer、Christopher R. Jones、Timothy J. Miles

  DOI：10.1021/ol302541j

  日期：2012.11.2

  The asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO4 catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde.

  描述了γ-内酰胺β-内酯抗生素恶唑霉素A的关键吡咯烷酮核心（包括高度复杂的环外碳链）的不对称合成。主要特征包括芳香族吡咯核的桦木还原，后期RuO 4催化的吡咯烷氧化以及对醛的高度非对映选择性有机铈。
• Total Synthesis of Neooxazolomycin
  作者：Evans Otieno Onyango、Joji Tsurumoto、Naoko Imai、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1002/anie.200702229

  日期：2007.9.3
• Stereoselective synthesis of the right-hand cores of 16-methylated oxazolomycins
  作者：Kohei Eto、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1016/j.tet.2017.12.036

  日期：2018.2

  The right-hand heterocyclic cores of oxazolomycins having either 16R or 16S-methyl group configurations on the beta-lactones were stereoselectively synthesized from the common intermediate utilized for our previous syntheses of neooxazolomycin and oxazolomycin A. In addition, the right-hand segment required for the synthesis of KSM-2690 and lajollamycin members was also synthesized in a stereo-selective manner. (C) 2017 Elsevier Ltd. All rights reserved.