1-methylidenesqualene | 122333-76-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-methylidenesqualene
• 英文别名: 3,7,11,16,20,24-Hexamethyl-pentacosa-1,3,7,11,15,19,23-heptaene；(3E,7E,11E,15E,19E)-3,7,11,16,20,24-hexamethylpentacosa-1,3,7,11,15,19,23-heptaene
• CAS: 122333-76-0
• 化学式: C₃₁H₅₀
• 分子量: 422.738
• InChiKey: YFJDHPRKGJEVKR-RLEGVFPPSA-N

物化性质

• 沸点：
  511.5±45.0 °C(Predicted)
• 密度：
  0.852±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methylidenesqualene 在 Na-citrate buffer 、 recombinant A_. acidocaldarius SHC 作用下， 反应 16.0h， 以35%的产率得到30-methylidene-hop-22(29)-ene
  参考文献：
  名称：

  1-Methylidenesqualene and 25-Methylidenesqualene as Active-Site Probes for Bacterial Squalene:Hopene Cyclase

  摘要：

  1-Methylidenesqualene and 25-methylidenesqualene were converted to 30-methylidenehop-22(29)-ene by squalene:hopene cyclase from Alicyclobacillus acidocaidarius. It was remarkable that both analogues generated the same product. The hopanyl intermediate cation, stabilized by the methylidene residue, enabled a rotation of the isobutenyl group at C-21 prior to the final proton elimination. In contrast, in the formation of hop-22(29)-ene, the final proton abstraction takes place regiospecifically from the Z-methyl group, which was verified by cyclization of (1,1,1,24,24,24-H-2(6))squalene into (23,23,23,30,30,30-H-2(6))hop-22(29)-ene.

  DOI：

  10.1021/ol036509r
• 作为产物：
  描述：

  角鲨烯 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 正丁基锂 、 selenium(IV) oxide 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 1-methylidenesqualene
  参考文献：
  名称：

  含有异亚丙基的角鲨烯类似物可作为猪肝角鲨烯环氧化酶和氧化角鲨烯环化酶的潜在抑制剂。

  摘要：

  合成了几种含有1，1-二卤代烯烃，乙炔，丙二烯，二烯和环丙烷官能团的角鲨烯类似物，并将其评估为猪肝角鲨烯环氧化酶和氧化角鲨烯环化酶的潜在抑制剂。制备了单功能和双功能的类似物。对于大多数化合物（IC50远远大于400 microM），发现对角鲨烯环氧酶和氧化角鲨烯环化酶的抑制作用较弱，但单官能炔醇（IC50 = 300 microM）除外。该炔醇表现出混合功能抑制，KI = 0.95 mM。醇氧化为炔酮会导致环氧酶活性降低，表明羟基对于抑制作用是必需的，并且炔醇不是前抑制剂。分子力学计算表明，好的抑制剂应在非极化的不饱和体系上具有疏水性取代基。另外，前C-3羟基的存在可以赋予抑制效力。

  DOI：

  10.1021/jm00129a022

文献信息

• SEN, STEPHANIE E.;PRESTWICH, GLENN D., J. MED. CHEM., 32,(1989) N, C. 2152-2158
  作者：SEN, STEPHANIE E.、PRESTWICH, GLENN D.

  DOI：——

  日期：——
• Squalene analogs containing isopropylidene mimics as potential inhibitors of pig liver squalene epoxidase and oxidosqualene cyclase
  作者：Stephanie E. Sen、Glenn D. Prestwich

  DOI：10.1021/jm00129a022

  日期：1989.9

  Several squalene analogues containing 1,1-dihaloalkene, acetylene, allene, diene, and cyclopropane functionalities were synthesized and evaluated as potential inhibitors of pig liver squalene epoxidase and oxidosqualene cyclase. Both monofunctionalized and bisfunctionalized analogues were prepared. Poor inhibition of squalene epoxidase and oxidosqualene cyclase was found for most compounds (IC50 much

  合成了几种含有1，1-二卤代烯烃，乙炔，丙二烯，二烯和环丙烷官能团的角鲨烯类似物，并将其评估为猪肝角鲨烯环氧化酶和氧化角鲨烯环化酶的潜在抑制剂。制备了单功能和双功能的类似物。对于大多数化合物（IC50远远大于400 microM），发现对角鲨烯环氧酶和氧化角鲨烯环化酶的抑制作用较弱，但单官能炔醇（IC50 = 300 microM）除外。该炔醇表现出混合功能抑制，KI = 0.95 mM。醇氧化为炔酮会导致环氧酶活性降低，表明羟基对于抑制作用是必需的，并且炔醇不是前抑制剂。分子力学计算表明，好的抑制剂应在非极化的不饱和体系上具有疏水性取代基。另外，前C-3羟基的存在可以赋予抑制效力。
• 1-Methylidenesqualene and 25-Methylidenesqualene as Active-Site Probes for Bacterial Squalene:Hopene Cyclase
  作者：Hideya Tanaka、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1021/ol036509r

  日期：2004.3.1

  1-Methylidenesqualene and 25-methylidenesqualene were converted to 30-methylidenehop-22(29)-ene by squalene:hopene cyclase from Alicyclobacillus acidocaidarius. It was remarkable that both analogues generated the same product. The hopanyl intermediate cation, stabilized by the methylidene residue, enabled a rotation of the isobutenyl group at C-21 prior to the final proton elimination. In contrast, in the formation of hop-22(29)-ene, the final proton abstraction takes place regiospecifically from the Z-methyl group, which was verified by cyclization of (1,1,1,24,24,24-H-2(6))squalene into (23,23,23,30,30,30-H-2(6))hop-22(29)-ene.