benzyl (4S)-2,2-dimethyl-4-[(4-oxo-3-phenoxycyclohex-2-en-1-yl)methyl]-1,3-oxazolidine-3-carboxylate | 222027-29-4

• 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: benzyl (4S)-2,2-dimethyl-4-[(4-oxo-3-phenoxycyclohex-2-en-1-yl)methyl]-1,3-oxazolidine-3-carboxylate
• CAS: 222027-29-4
• 化学式: C₂₆H₂₉NO₅
• 分子量: 435.52
• InChiKey: GRUSQABTLKWJLA-LBAQZLPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-2,2-dimethyl-4-[(4-oxo-3-phenoxycyclohex-2-en-1-yl)methyl]-1,3-oxazolidine-3-carboxylate 在 吡啶 、 苯基氯化硒 、 双氧水 、 potassium carbonate 作用下， 生成 N-benzyloxycarbonyl-N,O-isopropylidenyl-3-phenoxy-(S)-tyrosinol
  参考文献：
  名称：

  A synthetic approach to diaryl ethers using the Robinson annulation

  摘要：

  An alternative synthetic approach to diaryl ethers has been developed. In the key transformation, Robinson annulation of nonracemic aldehydes 16a,b, derived from L-glutamic acid 5-methyl ester and phenoxymethylvinyl ketone, provided alpha-phenoxyenones 17a,b. The Cbz-protected oxazolidine 17b was further converted into the diaryl ether 18b utilizing an oxidative selenation protocol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00466-2
• 作为产物：
  描述：

  (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 在 吗啉 、 sodium tetrahydroborate 、 4 A molecular sieve 、 水 、 二异丁基氢化铝 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 1.0h， 生成 benzyl (4S)-2,2-dimethyl-4-[(4-oxo-3-phenoxycyclohex-2-en-1-yl)methyl]-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  A synthetic approach to diaryl ethers using the Robinson annulation

  摘要：

  An alternative synthetic approach to diaryl ethers has been developed. In the key transformation, Robinson annulation of nonracemic aldehydes 16a,b, derived from L-glutamic acid 5-methyl ester and phenoxymethylvinyl ketone, provided alpha-phenoxyenones 17a,b. The Cbz-protected oxazolidine 17b was further converted into the diaryl ether 18b utilizing an oxidative selenation protocol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00466-2

文献信息

• A synthetic approach to diaryl ethers using the Robinson annulation
  作者：Xianqi Feng、Eric D. Edstrom

  DOI：10.1016/s0957-4166(98)00466-2

  日期：1999.1

  An alternative synthetic approach to diaryl ethers has been developed. In the key transformation, Robinson annulation of nonracemic aldehydes 16a,b, derived from L-glutamic acid 5-methyl ester and phenoxymethylvinyl ketone, provided alpha-phenoxyenones 17a,b. The Cbz-protected oxazolidine 17b was further converted into the diaryl ether 18b utilizing an oxidative selenation protocol. (C) 1999 Elsevier Science Ltd. All rights reserved.