2,2-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-4-tetradec-(E)-ylidene-tetrahydro-furan | 220025-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-4-tetradec-(E)-ylidene-tetrahydro-furan
• CAS: 220025-17-2
• 化学式: C₅₂H₇₄O₃Si₂
• 分子量: 803.329
• InChiKey: WUDKFIXSQIDNAX-ZHPLTJAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.93
• 重原子数：
  57.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-4-tetradec-(E)-ylidene-tetrahydro-furan 在 二正丁基氧化锡 、 triethylamine tris(hydrogen fluoride) 作用下， 生成 Acetic acid 2-hydroxymethyl-4-tetradec-(Z)-ylidene-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Conformationally constrained analogues of diacylglycerol (DAG). 15.1 The indispensable role of the sn-1 and sn-2 carbonyls in the binding of DAG-lactones to protein kinase C (PK-C)

  摘要：

  The binding mode of DAG-lactones to PK-C was investigated using the C1b domain from the Xray structure of the phorbol ester/C1b complex of PK-C delta as a template. Modeling experiments revealed two binding alternatives in which one of the carbonyls of the DAG lactones remained uninvolved with the protein. Experimentally, however, the removal of either sn-1 or sn-2 carbonyls caused a dramatic drop in binding affinity towards PK-C. Although it was not possible to discriminate between the two binding alternatives of the DAG-lactones, the study demonstrates an important role for the additional carbonyl group. The function of this group could be equivalent to that of the C-9(OH)/C-13 (C=O) motif in phorbol esters, which also appears free of interactions in the phorbol ester/C1b complex. This role presumably reflects interaction with the phosholipid head groups required for high affinity binding under the conditions of the biological assays. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00614-3
• 作为产物：
  描述：

  2,2-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-tetradec-(Z)-ylidene-tetrahydro-furan 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 生成 2,2-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-4-tetradec-(E)-ylidene-tetrahydro-furan
  参考文献：
  名称：

  Conformationally constrained analogues of diacylglycerol (DAG). 15.1 The indispensable role of the sn-1 and sn-2 carbonyls in the binding of DAG-lactones to protein kinase C (PK-C)

  摘要：

  The binding mode of DAG-lactones to PK-C was investigated using the C1b domain from the Xray structure of the phorbol ester/C1b complex of PK-C delta as a template. Modeling experiments revealed two binding alternatives in which one of the carbonyls of the DAG lactones remained uninvolved with the protein. Experimentally, however, the removal of either sn-1 or sn-2 carbonyls caused a dramatic drop in binding affinity towards PK-C. Although it was not possible to discriminate between the two binding alternatives of the DAG-lactones, the study demonstrates an important role for the additional carbonyl group. The function of this group could be equivalent to that of the C-9(OH)/C-13 (C=O) motif in phorbol esters, which also appears free of interactions in the phorbol ester/C1b complex. This role presumably reflects interaction with the phosholipid head groups required for high affinity binding under the conditions of the biological assays. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00614-3