(+/-)-7-phenylhept-1-en-4-ol | 273747-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-7-phenylhept-1-en-4-ol
• 英文别名: 7-Phenylhept-1-en-4-ol
• CAS: 273747-66-3
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: MQYUIFVVECTVIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  三异丙基氯硅烷 、 (+/-)-7-phenylhept-1-en-4-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到(+/-)-triisopropyl{[1-(3-phenylpropyl)but-3-enyl]oxy}silane
  参考文献：
  名称：

  Chemoselective Cross Metathesis of Bishomoallylic Alcohols:  Rapid Access to Fragment A of the Cryptophycins

  摘要：

  The racemic or enantioselective allylation of in situ formed beta,gamma-unsaturated aldehydes provides efficient access to bishomoallylic alcohols from readily available 2-vinyloxiranes. These products, when subjected to modified Grubbs cross metathesis conditions, afforded terminally homologated products in moderate to good yields with high E selectivity and without degradation of the enantiomeric excess. The compounds obtained through this two-step sequence yield fragments of an important and pharmacologically active family of cryptophycins.

  DOI：

  10.1021/ol049883f
• 作为产物：
  描述：

  4-苯基丁醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (+/-)-7-phenylhept-1-en-4-ol
  参考文献：
  名称：

  Chemoselective Cross Metathesis of Bishomoallylic Alcohols:  Rapid Access to Fragment A of the Cryptophycins

  摘要：

  The racemic or enantioselective allylation of in situ formed beta,gamma-unsaturated aldehydes provides efficient access to bishomoallylic alcohols from readily available 2-vinyloxiranes. These products, when subjected to modified Grubbs cross metathesis conditions, afforded terminally homologated products in moderate to good yields with high E selectivity and without degradation of the enantiomeric excess. The compounds obtained through this two-step sequence yield fragments of an important and pharmacologically active family of cryptophycins.

  DOI：

  10.1021/ol049883f

文献信息

• Acid-Promoted Prins Cyclizations of Enol Ethers To Form Tetrahydropyrans
  作者：David J. Hart、Chad E. Bennett

  DOI：10.1021/ol0342756

  日期：2003.5.1

  Trifluoroacetic acid efficiently catalyzes Prins cyclizations of enol ethers 8 to provide tetrahydropyrans 9 and 10. These tetrahydropyrans are isolated with combined yields of 42-85% and stereoselectivities at C(4) ranging from 95:5 to 50:50 depending on the nature of the substituent R. Unique byproducts of these cyclizations that reveal the presence of underlying equilibria have been isolated and

  三氟乙酸可有效催化烯醇醚8的Prins环化反应，提供四氢吡喃9和10。根据四氢吡喃的性质，分离得到的四氢吡喃的合并收率为42-85％，C（4）的立体选择性范围为95：5至50:50。这些环化作用的独特副产物显示出潜在的平衡性已被分离和鉴定。[反应：看文字]
• Brenna, Elisabetta; Scaramelli, Laura; Serra, Stefano, Synlett, 2000, # 3, p. 357 - 358
  作者：Brenna, Elisabetta、Scaramelli, Laura、Serra, Stefano

  DOI：——

  日期：——
• Chemoselective Cross Metathesis of Bishomoallylic Alcohols:  Rapid Access to Fragment A of the Cryptophycins
  作者：Mark Lautens、Matthew L. Maddess

  DOI：10.1021/ol049883f

  日期：2004.6.1

  The racemic or enantioselective allylation of in situ formed beta,gamma-unsaturated aldehydes provides efficient access to bishomoallylic alcohols from readily available 2-vinyloxiranes. These products, when subjected to modified Grubbs cross metathesis conditions, afforded terminally homologated products in moderate to good yields with high E selectivity and without degradation of the enantiomeric excess. The compounds obtained through this two-step sequence yield fragments of an important and pharmacologically active family of cryptophycins.