11-oxabicyclo[5.3.1]undecan-1-ol | 1192431-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 11-oxabicyclo[5.3.1]undecan-1-ol
• 英文别名: 11-Oxabicyclo[5.3.1]undecan-1-ol
• CAS: 1192431-30-3
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: OCIGLZKNCVWLAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-oxabicyclo[5.3.1]undecan-1-ol 在 对甲苯磺酸 作用下， 90.0~120.0 ℃ 、3.0 kPa 条件下， 生成 11-oxabicyclo[5.3.1]undec-1-ene 、 11-Oxabicyclo[5.3.1]undec-1(10)-ene
  参考文献：
  名称：

  Transformation of Hydroxycycloalkanones to Oxabicycloalkenes

  摘要：

  Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.

  DOI：

  10.3987/com-09-11728
• 作为产物：
  描述：

  环癸烷 在 ferredoxin reductase 、 [2Fe–2S] ferredoxin 、 cytochrome P₄₅₀ enzyme CYP₁₀₁B₁ 、 cytochrome P₄₅₀ enzyme CYP₁₀₁C₁ 作用下， 以 aq. buffer 为溶剂， 生成 6-羟基环癸烷-1-酮 、 11-oxabicyclo[5.3.1]undecan-1-ol 、 5-hydroxycyclodecanone 、 11-oxabicyclo[4.4.1]undecan-1-ol
  参考文献：
  名称：

  相同家族的两种细胞色素P450酶对烃衍生物的互补和选择性氧化

  摘要：

  细胞色素P450酶CYP101B1和CYP101C1，来自细菌新孢子虫DSM12444可高活性和选择性地羟基化类异戊二烯。为了扩展和建立其底物范围，以开发应用，研究了选择环烷烃，酮和醇的氧化。环烷被氧化，但两种酶均显示出中等的结合亲和力和较低的生产活性。我们通过将组氨酸残基切换为苯丙氨酸（H85F），使活性位点更具疏水性，从而改善了这些底物与CYP101B1的结合和活性。环烷烃骨架中酮部分的存在显着改善了两种酶的氧化活性。CYP101C1优选在C-2位置催化环烷酮的氧化，而CYP101B1在远离羰基的位置以较高的生产率氧化这些底物。这表明每种酶的活性位点中环酮的结合方向必须不同。线性酮也被两种酶氧化，但活性和选择性较低。CYP101B1比CYP101C1更有效地氧化具有酯导向基团的环状底物。两种酶都在远离酯导向基团的环系统上以高区域选择性催化这些酯的氧化。CYP101C1比CYP101B1

  DOI：

  10.1039/d0cy01040e

文献信息

• Selective biocatalytic hydroxylation of unactivated methylene C–H bonds in cyclic alkyl substrates
  作者：Md Raihan Sarkar、Samrat Dasgupta、Simon M. Pyke、Stephen G. Bell

  DOI：10.1039/c9cc02060h

  日期：——

  The cytochrome P450 monooxygenase CYP101B1 from Novosphingobium aromaticivorans selectively hydroxylated methylene C–H bonds in cycloalkyl rings. Cycloketones and cycloalkyl esters containing C6, C8, C10 and C12 rings were oxidised with high selectively on the opposite side of the ring to the carbonyl substituent. Cyclodecanone was oxidised to oxabicycloundecanol derivatives in equilibrium with the

  从细胞色素P450单加氧酶CYP101B1 Novosphingobium芳烃选择性羟基化亚甲基在环烷基环的C-H键。含有C6，C8，C10和C12环的环酮和环烷基酯在环上与羰基取代基相反的一侧被高选择性地氧化。环十二烷酮被氧化成与羟基环癸烷平衡的氧杂环十一烷醇衍生物。
• Transformation of Hydroxycycloalkanones to Oxabicycloalkenes
  作者：Herbert Meier、Guido Krämer、Heiner Detert

  DOI：10.3987/com-09-11728

  日期：——

  Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.
• Complementary and selective oxidation of hydrocarbon derivatives by two cytochrome P450 enzymes of the same family
  作者：Md. Raihan Sarkar、Stephen G. Bell

  DOI：10.1039/d0cy01040e

  日期：——

  The cytochrome P450 enzymes CYP101B1 and CYP101C1, which are from the bacterium Novosphingobium aromaticivorans DSM12444, can hydroxylate norisoprenoids with high activity and selectivity. With the goal of expanding and establishing their substrate range with a view to developing applications, the oxidation of a selection of cyclic alkanes, ketones and alcohols was investigated. Cycloalkanes were oxidised

  细胞色素P450酶CYP101B1和CYP101C1，来自细菌新孢子虫DSM12444可高活性和选择性地羟基化类异戊二烯。为了扩展和建立其底物范围，以开发应用，研究了选择环烷烃，酮和醇的氧化。环烷被氧化，但两种酶均显示出中等的结合亲和力和较低的生产活性。我们通过将组氨酸残基切换为苯丙氨酸（H85F），使活性位点更具疏水性，从而改善了这些底物与CYP101B1的结合和活性。环烷烃骨架中酮部分的存在显着改善了两种酶的氧化活性。CYP101C1优选在C-2位置催化环烷酮的氧化，而CYP101B1在远离羰基的位置以较高的生产率氧化这些底物。这表明每种酶的活性位点中环酮的结合方向必须不同。线性酮也被两种酶氧化，但活性和选择性较低。CYP101B1比CYP101C1更有效地氧化具有酯导向基团的环状底物。两种酶都在远离酯导向基团的环系统上以高区域选择性催化这些酯的氧化。CYP101C1比CYP101B1
• Total Synthesis of (−)-Lepistine
  作者：Yusuke Kitabayashi、Satoshi Yokoshima、Tohru Fukuyama

  DOI：10.1021/ol5010033

  日期：2014.6.6

  The first total synthesis of (-)-lepistine has been accomplished in 11 steps from (S)-glycidol. The synthesis features construction of the 10-membered ring via an intramolecular epoxide opening by nosylamide, regioselective dehydration to form an enol ether, and construction of the aminal moiety induced by cleavage of the nosyl groups.