3-Hydroxy-3-phenyl-3-styryl-propionsaeure-aethylester | 25409-21-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-Hydroxy-3-phenyl-3-styryl-propionsaeure-aethylester
• 英文别名: Ethyl 3-hydroxy-3,5-diphenylpent-4-enoate
• CAS: 25409-21-6
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: ULMPZGPNBRSWPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-3-phenyl-3-styryl-propionsaeure-aethylester 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 0.84h， 生成
  参考文献：
  名称：

  通过逻辑底物设计控制乙烯基离子的分子拓扑：线性和2,4-二烯醛的高区域和立体选择性氨基催化1,6-加成

  摘要：

  有关拓扑控制的所有内容：标题反应可产生有价值的四氢呋喃螺硫醇（参见方案； TMS =三甲基甲硅烷基），并例举了罕见的不对称1,6加成反应，对线性2,4二烯进行高δ位和立体选择性的过程。β-二烯基位置上的一个转向基团确保了催化活性的乙烯基亚胺基离子中间体的分子预组织，从而可高度预测反应结果。

  DOI：

  10.1002/anie.201305870
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 碘 、 sodium hydroxide 、 锌 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 3-Hydroxy-3-phenyl-3-styryl-propionsaeure-aethylester
  参考文献：
  名称：

  Vinylogous有机催化三级联反应：在复杂的螺-氧环己烷中锻造六个立体中心。

  摘要：

  AbstractWe report a triple vinylogous cascade reaction, yielding valuable spiro‐oxindolic cyclohexane derivatives. The three‐component domino process proceeds by way of a catalyzed Michael/1,6‐addition/vinylogous aldol sequence affording the products with six stereogenic centers and very high control over the stereochemistry. The chemistry is based on a rare example of asymmetric 1,6‐addition to linear 2,4‐dienals proceeding with complete δ‐site selectivity. Key to the reaction development was a directing group positioned at the β‐dienal position, which was essential for achieving highly predictable reaction outcomes.magnified image

  DOI：

  10.1002/adsc.201300667

文献信息

• PROCESS FOR PRODUCING FUSED IMIDAZOLE COMPOUND, REFORMATSKY REAGENT IN STABLE FORM, AND PROCESS FOR PRODUCING THE SAME
  申请人：Kawakami Jun-Ichi

  公开号：US20100105922A1

  公开（公告）日：2010-04-29

  The present invention provides an industrially advantageous process for producing a steroid C 17,20 lyase inhibitor represented by the general formula (I); and a Reformatsky reagent in a stable form suitable for the process. In the present invention, a compound represented by the general formula (I) is produced by reducing a specific β-hydroxy ester compound derivative or a salt thereof obtained from a specific carbonyl compound in a Reformatsky reaction in the presence of a metal hydride complex and a metal halide, and then subjecting it to a ring-closing reaction. In the above Reformatsky reaction, it is useful to use a stable solution of a compound represented by the general formula BrZnCH 2 COOC 2 H 5 or a crystal of the compound which is represented by the formula (BrZnCH 2 COOC 2 H 5 .THF) 2 .

  本发明提供了一种工业上有利的生产类固醇C17,20裂解酶抑制剂的过程，该抑制剂由通式（I）表示；以及适用于该过程的稳定形式的Reformatsky试剂。在本发明中，通过在金属氢化物复合物和金属卤化物的存在下还原从特定羰基化合物中获得的特定β-羟基酯化合物衍生物或其盐，并随后将其进行环合反应，从而产生通式（I）表示的化合物。在上述Reformatsky反应中，使用通式BrZnCH2COOC2H5表示的化合物的稳定溶液或者由式（BrZnCH2COOC2H5.THF）2表示的化合物的晶体是有用的。
• Reformatsky Reagent in Stable Form and Process for Producing the Same
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2275411A2

  公开（公告）日：2011-01-19

  The present invention provides an industrially advantageous process for producing a steroid C17,20 lyase inhibitor represented by the general formula (I): and a Reformatsky reagent in a stable form suitable for the process. In the present invention, a compound represented by the general formula (I) is produced by reducing a specific β-hydroxy ester compound derivative or a salt thereof obtained from a specific carbonyl compound in a Reformatsky reaction in the presence of a metal hydride complex and a metal halide, and then subjecting it to a ring-closing reaction. In the above Reformatsky reaction, it is useful to use a stable solution of a compound represented by the general formula BrZnCH2COOC2H5 or a crystal of the compound which is represented by the formula (BrZnCH2COOC2H5·THF)2.

  本发明提供了一种生产由通式（I）代表的类固醇 C17,20 裂解酶抑制剂的工业化有利工艺： 和一种适用于该工艺的稳定形式的 Reformatsky 试剂。 在本发明中，在金属氢化物络合物和金属卤化物存在下，通过 Reformatsky 反应还原特定 β-羟基酯化合物衍生物或由特定羰基化合物得到的其盐，然后使其进行闭环反应，即可制得通式（I）代表的化合物。在上述 Reformatsky 反应中，使用通式为 BrZnCH2COOC2H5 的化合物的稳定溶液或通式为 (BrZnCH2COOC2H5-THF)2 的化合物晶体是有用的。
• Cure,J.; Gaudemar,M., Bulletin de la Societe Chimique de France, 1969, p. 2471 - 2476
  作者：Cure,J.、Gaudemar,M.

  DOI：——

  日期：——
• US8093403B2
  申请人：——

  公开号：US8093403B2

  公开（公告）日：2012-01-10
• Vinylogous Organocatalytic Triple Cascade Reaction: Forging Six Stereocenters in Complex Spiro-Oxindolic Cyclohexanes
  作者：Indranil Chatterjee、David Bastida、Paolo Melchiorre

  DOI：10.1002/adsc.201300667

  日期：2013.11.11

  AbstractWe report a triple vinylogous cascade reaction, yielding valuable spiro‐oxindolic cyclohexane derivatives. The three‐component domino process proceeds by way of a catalyzed Michael/1,6‐addition/vinylogous aldol sequence affording the products with six stereogenic centers and very high control over the stereochemistry. The chemistry is based on a rare example of asymmetric 1,6‐addition to linear 2,4‐dienals proceeding with complete δ‐site selectivity. Key to the reaction development was a directing group positioned at the β‐dienal position, which was essential for achieving highly predictable reaction outcomes.magnified image