(+/-)-ethyl (E)-4-t-butyldiphenylsiloxy-2-cyclopentenylideneacetate | 329363-21-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+/-)-ethyl (E)-4-t-butyldiphenylsiloxy-2-cyclopentenylideneacetate
• 英文别名: ethyl (2E)-2-[4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-ylidene]acetate
• CAS: 329363-21-5
• 化学式: C₂₅H₃₀O₃Si
• 分子量: 406.597
• InChiKey: VGWNSVKGNRNYGM-VXPUYCOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl (E)-4-t-butyldiphenylsiloxy-2-cyclopentenylideneacetate 在 potassium carbonate 三乙烯二胺 、 盐酸 、 四氧化锇 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 140.0h， 生成 (+/-)-(E)-[2(R),3(S),4(R)]-trihydroxycyclopentylideneacetic acid
  参考文献：
  名称：

  Five-Membered Ring Analogues of Shikimic Acid

  摘要：

  Shikimate and other intermediates of the shikimate-chorismate pathway are densely functionalized structures that seem to offer Limited options for skeletal modification. We designed and synthesized cyclopentylidenes 1 and 2, as well as cyclopentenes 3 and 4, as novel ring-contracted analogues of shikimic acid. Enzymatic studies showed that analogues 1-3 are indeed processed by shikimate kinase to give phosphates I-P, 2-P, and 3-P as five-membered ring analogues of shikimate-3-phosphate. In particular, analogue 1 is converted by the enzyme at a rate only 3.5-fold slower than that of the native substrate, while analogue 3 binds to shikimate kinase with an apparent K-m of 1.7 mM, compared to 0.14 mM for shikimate.

  DOI：

  10.1021/jo001121k
• 作为产物：
  描述：

  4-benzoyloxy-2-cyclopentenone 在 咪唑 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.5h， 生成 (+/-)-ethyl (E)-4-t-butyldiphenylsiloxy-2-cyclopentenylideneacetate
  参考文献：
  名称：

  Five-Membered Ring Analogues of Shikimic Acid

  摘要：

  Shikimate and other intermediates of the shikimate-chorismate pathway are densely functionalized structures that seem to offer Limited options for skeletal modification. We designed and synthesized cyclopentylidenes 1 and 2, as well as cyclopentenes 3 and 4, as novel ring-contracted analogues of shikimic acid. Enzymatic studies showed that analogues 1-3 are indeed processed by shikimate kinase to give phosphates I-P, 2-P, and 3-P as five-membered ring analogues of shikimate-3-phosphate. In particular, analogue 1 is converted by the enzyme at a rate only 3.5-fold slower than that of the native substrate, while analogue 3 binds to shikimate kinase with an apparent K-m of 1.7 mM, compared to 0.14 mM for shikimate.

  DOI：

  10.1021/jo001121k

文献信息

• Five-Membered Ring Analogues of Shikimic Acid
  作者：Ming An、Tab Toochinda、Paul A. Bartlett

  DOI：10.1021/jo001121k

  日期：2001.2.1

  Shikimate and other intermediates of the shikimate-chorismate pathway are densely functionalized structures that seem to offer Limited options for skeletal modification. We designed and synthesized cyclopentylidenes 1 and 2, as well as cyclopentenes 3 and 4, as novel ring-contracted analogues of shikimic acid. Enzymatic studies showed that analogues 1-3 are indeed processed by shikimate kinase to give phosphates I-P, 2-P, and 3-P as five-membered ring analogues of shikimate-3-phosphate. In particular, analogue 1 is converted by the enzyme at a rate only 3.5-fold slower than that of the native substrate, while analogue 3 binds to shikimate kinase with an apparent K-m of 1.7 mM, compared to 0.14 mM for shikimate.