3-(tert-butoxycarbonyloxy)-3-phenylpropanoic acid | 906551-88-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(tert-butoxycarbonyloxy)-3-phenylpropanoic acid
• 英文别名: 3-[(2-Methylpropan-2-yl)oxycarbonyloxy]-3-phenylpropanoic acid；3-[(2-methylpropan-2-yl)oxycarbonyloxy]-3-phenylpropanoic acid
• CAS: 906551-88-0
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: XLYZSEKAIJZZDS-UHFFFAOYSA-N

物化性质

• 熔点：
  108-111 °C
• 沸点：
  374.4±35.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(tert-butoxycarbonyloxy)-3-phenylpropanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以100%的产率得到3-羟基-3-苯丙酸
  参考文献：
  名称：

  Highly anti-Selective Catalytic Aldol Reactions of Amides with Aldehydes

  摘要：

  Barium phenoxide-catalyzed, highly anti-selective direct-type aldol reactions of amides with aldehydes have been developed. In the presence of a slight excess amount of an amide, the desired reactions proceeded smoothly under mild conditions, and a wide range of aromatic, heterocyclic, alpha,beta-unsaturated aldehydes were applicable to afford the desired adducts in high yields with high anti-selectivities. A catalytic, enantioselective reaction of an amide with an aldehyde using a chiral ligand is also described.

  DOI：

  10.1021/ja061221t
• 作为产物：
  描述：

  tert-butyl acetyl(4-methoxyphenyl)carbamate 在 barium tert-butoxide 、 乙酸酐 、 溶剂黄146 、 4-甲氧基苯酚 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 54.0h， 生成 3-(tert-butoxycarbonyloxy)-3-phenylpropanoic acid
  参考文献：
  名称：

  Highly anti-Selective Catalytic Aldol Reactions of Amides with Aldehydes

  摘要：

  Barium phenoxide-catalyzed, highly anti-selective direct-type aldol reactions of amides with aldehydes have been developed. In the presence of a slight excess amount of an amide, the desired reactions proceeded smoothly under mild conditions, and a wide range of aromatic, heterocyclic, alpha,beta-unsaturated aldehydes were applicable to afford the desired adducts in high yields with high anti-selectivities. A catalytic, enantioselective reaction of an amide with an aldehyde using a chiral ligand is also described.

  DOI：

  10.1021/ja061221t

文献信息

• Highly <i>a</i><i>nti</i>-Selective Catalytic Aldol Reactions of Amides with Aldehydes
  作者：Susumu Saito、Shu Kobayashi

  DOI：10.1021/ja061221t

  日期：2006.7.1

  Barium phenoxide-catalyzed, highly anti-selective direct-type aldol reactions of amides with aldehydes have been developed. In the presence of a slight excess amount of an amide, the desired reactions proceeded smoothly under mild conditions, and a wide range of aromatic, heterocyclic, alpha,beta-unsaturated aldehydes were applicable to afford the desired adducts in high yields with high anti-selectivities. A catalytic, enantioselective reaction of an amide with an aldehyde using a chiral ligand is also described.