(1R-(1α,5α,6α))-6-(2-propyl)-3-oxabicyclo[3.1.0]hexan-2-one | 149859-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R-(1α,5α,6α))-6-(2-propyl)-3-oxabicyclo[3.1.0]hexan-2-one
• 英文别名: (1R,5S,6R)-6-propan-2-yl-3-oxabicyclo[3.1.0]hexan-2-one
• CAS: 149859-30-3
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: DOZAHNDBGHYQKG-XVMARJQXSA-N

物化性质

• 沸点：
  233.8±8.0 °C(predicted)
• 密度：
  1.102±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R-(1α,5α,6α))-6-(2-propyl)-3-oxabicyclo[3.1.0]hexan-2-one 在 三甲基铝 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 生成 N-<(1R-(1α,2α,3α))-2-formyl-3-(2-propyl)cyclopropanoyl>-N'-(p-methoxybenzyl)-O-methyl-L-tyrosine-N-methylamide
  参考文献：
  名称：

  Cyclopropanes as conformationally restricted peptide isosteres. Design and synthesis of novel collagenase inhibitors

  摘要：

  The 1,2,3-trisubstituted cyclopropane derivatives 9 and 10 were prepared as conformationally constrained analogues of the known collagenase inhibitor 8. The syntheses of 9 and 10 featured the highly enantioselective Rh2[S-MEPY]4 catalyzed cyclization of the, allylic diazo ester 11 to give the lactone 13. Opening of the lactone ring of 13 with N,O-di-(p-methoxybenzyl)hydroxylamine under Weinreb conditions followed by refunctionalization, coupling of the intermediate acid 16 with 17 and deprotection led to the dipeptide analogue 9. Alternatively, the lactone ring of 13 could be opened with the protected tyrosine 21 by a novel variant of the Weinreb protocol to give directly the dipeptide analogue 22 which was then converted into 10.

  DOI：

  10.1016/s0040-4020(01)90212-1
• 作为产物：
  描述：

  (Z)-4-methylpent-2-en-1-ol 在 Rh₂[5S-MEPY]4 、 N,N-二甲基苯胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (1R-(1α,5α,6α))-6-(2-propyl)-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  使用手性二铑 (II) 甲酰胺催化剂对烯丙基和高烯丙基重氮乙酸酯和重氮乙酰胺进行对映选择性分子内环丙烷化

  摘要：

  手性二铑 (I1) 四[2-吡咯烷酮-S(S)-羧酸甲酯]、Rhz(SS-MEPY)4 (7) 及其对映异构体催化烯丙基和高烯丙基重氮乙酸酯 loa-p 和 22a-j 的重氮分解, Rhz(5RMEPY)4 (S)，产生相应的分子内环丙烷化产物 lla-p 和 23a-j，产率良好至极好，并具有出色的对映选择性。使用烯丙基重氮乙酸盐观察到比使用它们的同型烯丙基对应物更高的对映控制，但是随着碳-碳双键上的取代模式的变化，烯丙基重氮乙酸盐的对映选择性变化更大。例如，3-烷基/芳基-2(Z)-链烯-1-y1重氮乙酸酯的分子内环丙烷化反应的对映选择性通常为194%，而同源的 4-烷基/芳基-3(Z)-烯1-基重氮乙酸酯的环化通常在 70-90% ee 的范围内。相应的 3-alkyYaryl-2(E)-alken-1-y1 和 4-烷基/芳基-3(E)-alken-1-yl 重氮乙酸酯发生环化，ee

  DOI：

  10.1021/ja00126a016

文献信息

• Iodocyclopropanes as versatile intermediates for the synthesis of substituted cyclopropanes
  作者：Stephen F. Martin、Michael P. Dwyer

  DOI：10.1016/s0040-4039(98)00072-0

  日期：1998.3

  Iodocyclopropanes are versatile synthetic intermediates that have been used to prepare a variety of alkyl, aryl and acyl substituted cyclopropanes via organometallic reactions.

  碘代环丙烷是通用的合成中间体，已用于通过有机金属反应制备各种烷基，芳基和酰基取代的环丙烷。
• Cyclopropanes as conformationally restricted peptide isosteres. Design and synthesis of novel collagenase inhibitors
  作者：Stephen F. Martin、Christopher J. Oalmann、Spiros Liras

  DOI：10.1016/s0040-4020(01)90212-1

  日期：1993.3

  The 1,2,3-trisubstituted cyclopropane derivatives 9 and 10 were prepared as conformationally constrained analogues of the known collagenase inhibitor 8. The syntheses of 9 and 10 featured the highly enantioselective Rh2[S-MEPY]4 catalyzed cyclization of the, allylic diazo ester 11 to give the lactone 13. Opening of the lactone ring of 13 with N,O-di-(p-methoxybenzyl)hydroxylamine under Weinreb conditions followed by refunctionalization, coupling of the intermediate acid 16 with 17 and deprotection led to the dipeptide analogue 9. Alternatively, the lactone ring of 13 could be opened with the protected tyrosine 21 by a novel variant of the Weinreb protocol to give directly the dipeptide analogue 22 which was then converted into 10.
• Enantioselective Intramolecular Cyclopropanations of Allylic and Homoallylic Diazoacetates and Diazoacetamides Using Chiral Dirhodium(II) Carboxamide Catalysts
  作者：Michael P. Doyle、Richard E. Austin、A. Scott Bailey、Michael P. Dwyer、Alexey B. Dyatkin、Alexey V. Kalinin、Michelle M. Y. Kwan、Spiros Liras、Christopher J. Oalmann

  DOI：10.1021/ja00126a016

  日期：1995.5

  counterparts, but allylic diazoacetates are subject to greater variations in enantioselectivities with changes in substitution patterns on the carbon-carbon double bond. For example, the enantioselectivities in the intramolecular cyclopropanations of 3-allcyl/aryl-2(Z)-alken-l-y1 diazoacetates are generally 194%, whereas the cyclizations of the homologous 4-alkyl/aryl-3(Z)-alken1-yl diazoacetates are typically

  手性二铑 (I1) 四[2-吡咯烷酮-S(S)-羧酸甲酯]、Rhz(SS-MEPY)4 (7) 及其对映异构体催化烯丙基和高烯丙基重氮乙酸酯 loa-p 和 22a-j 的重氮分解, Rhz(5RMEPY)4 (S)，产生相应的分子内环丙烷化产物 lla-p 和 23a-j，产率良好至极好，并具有出色的对映选择性。使用烯丙基重氮乙酸盐观察到比使用它们的同型烯丙基对应物更高的对映控制，但是随着碳-碳双键上的取代模式的变化，烯丙基重氮乙酸盐的对映选择性变化更大。例如，3-烷基/芳基-2(Z)-链烯-1-y1重氮乙酸酯的分子内环丙烷化反应的对映选择性通常为194%，而同源的 4-烷基/芳基-3(Z)-烯1-基重氮乙酸酯的环化通常在 70-90% ee 的范围内。相应的 3-alkyYaryl-2(E)-alken-1-y1 和 4-烷基/芳基-3(E)-alken-1-yl 重氮乙酸酯发生环化，ee