(3R^*,3aR^*,6aR^*)-tetrahydro-3-phenyl-1-(phenylmethyl)-1H,6H-furo<3,4-c>isoxazol-6-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R^*,3aR^*,6aR^*)-tetrahydro-3-phenyl-1-(phenylmethyl)-1H,6H-furo<3,4-c>isoxazol-6-one
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: UYMQWJSOHOIEGX-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-苄基羟胺 在 titanium(IV) isopropylate 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 5.0h， 生成 (3R^*,3aR^*,6aR^*)-tetrahydro-3-phenyl-1-(phenylmethyl)-1H,6H-furo<3,4-c>isoxazol-6-one
  参考文献：
  名称：

  Studies on tandem transesterification and intramolecular cycloaddition of nitrones. 1. Sequential bicyclization of α-methoxycarbonylnitrones with allyl alcohols

  摘要：

  Treatment of alpha-methoxycarbonylnitrones with 5 equiv. of allyl alcohols in the presence of 1 equiv. of titanium tetraisopropoxide causes tandem transesterification, E,Z-isomerization of the nitrone moieties, and intramolecular cycloaddition to afford bicyclized compounds in one step. To reduce amounts of allyl alcohol, combined use of a catalytic amount of titanium tetraisopropoxide and molecular sieves 4A was found to be a more improved catalytic system, It was also found that reactions of (Z)-allyl alcohols with alpha-methoxycarbonylnitrone ate more facile than those of (E)-allyl alcohols. This aspect was extended to geometry differentiated cycloaddition.

  DOI：

  10.1016/0040-4020(94)00874-t

文献信息

• One step bicyclization by way of tandem transesterification, intramolecular 1,3-dipolar cycloaddition of α-methoxycarbonylnitrones with allyl alcohols in the presence of titanium isopropoxide
  作者：Osamu Tamura、Tatsuya Yamaguchi、Katsuhide Noe、Masanori Sakamoto

  DOI：10.1016/s0040-4039(00)60602-0

  日期：1993.6

  Treatment of alpha-methoxycarbonylnitrones with allyl alcohols in the presence of titanium isopropoxide caused tandem transesterification, E,Z-isomerization and intramolecular cycloaddition to provide stereocontrolled polycyclic compounds in one step.
• Studies on tandem transesterification and intramolecular cycloaddition of nitrones. 1. Sequential bicyclization of α-methoxycarbonylnitrones with allyl alcohols
  作者：Osamu Tamura、Toshiyuki Okabe、Tatsuya Yamaguchi、Kentoku Gotanda、Katsuhide Noe、Masanori Sakamoto

  DOI：10.1016/0040-4020(94)00874-t

  日期：1995.1

  Treatment of alpha-methoxycarbonylnitrones with 5 equiv. of allyl alcohols in the presence of 1 equiv. of titanium tetraisopropoxide causes tandem transesterification, E,Z-isomerization of the nitrone moieties, and intramolecular cycloaddition to afford bicyclized compounds in one step. To reduce amounts of allyl alcohol, combined use of a catalytic amount of titanium tetraisopropoxide and molecular sieves 4A was found to be a more improved catalytic system, It was also found that reactions of (Z)-allyl alcohols with alpha-methoxycarbonylnitrone ate more facile than those of (E)-allyl alcohols. This aspect was extended to geometry differentiated cycloaddition.