tert-Butyl <(1S,4S,5R)-4-ethyl-2-oxo-5-phenylcyclopent-1-yl>acetate | 1026644-29-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-Butyl <(1S,4S,5R)-4-ethyl-2-oxo-5-phenylcyclopent-1-yl>acetate
• 英文别名: tert-butyl 2-[(1S,2R,3S)-3-ethyl-5-oxo-2-phenylcyclopentyl]acetate
• CAS: 1026644-29-0
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: KJQYZDGRWVLBCW-JOQOYGCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-Butyl <(1S,4S,5R)-4-ethyl-2-oxo-5-phenylcyclopent-1-yl>acetate 在 platinum(IV) oxide 、 N,N-二甲基甲酰胺 ruthenium trichloride 、 sodium periodate 、 草酰氯 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 28.0h， 生成 ((1S,2R,3S)-2-Chlorocarbonyl-3-ethyl-cyclopentyl)-acetic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of ionophore antibiotic X-14547 A (indanomycin)

  摘要：

  A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described. The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the ''left wing'' fragment 2. Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 --> 25 --> 26) via net S(N)2' coupling of [alpha-(mesyloxy)allyl]silanes with Grignard reagents catalyzed by CuCN. Salient features in the construction of the ''right wing'' subunit 3 include a modification of the Noyori three-component coupling procedure (32 --> 33) and the application,of a retro hetero Diels-Alder/intramolecular Diels-Alder (''mock Claisen'') process (5 --> 39), Palladium-mediated cross Coupling of ''left wing'' and ''right wing'' synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.

  DOI：

  10.1021/jo00081a010
• 作为产物：
  描述：

  tert-Butyl <(1S,4S,5R)-4-(tert-butyldimethylsiloxy)-2-oxo-5-phenylcyclopent-1-yl>acetate 在 吡啶 、 CuI*P(n-Bu)3 、 氢氟酸 、 甲基磺酰氯 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 3.25h， 生成 tert-Butyl <(1S,4S,5R)-4-ethyl-2-oxo-5-phenylcyclopent-1-yl>acetate
  参考文献：
  名称：

  Total synthesis of ionophore antibiotic X-14547 A (indanomycin)

  摘要：

  A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described. The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the ''left wing'' fragment 2. Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 --> 25 --> 26) via net S(N)2' coupling of [alpha-(mesyloxy)allyl]silanes with Grignard reagents catalyzed by CuCN. Salient features in the construction of the ''right wing'' subunit 3 include a modification of the Noyori three-component coupling procedure (32 --> 33) and the application,of a retro hetero Diels-Alder/intramolecular Diels-Alder (''mock Claisen'') process (5 --> 39), Palladium-mediated cross Coupling of ''left wing'' and ''right wing'' synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.

  DOI：

  10.1021/jo00081a010