2-(Hydroxy-thiophen-3-yl-methyl)-acrylic acid ethyl ester | 652980-13-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-(Hydroxy-thiophen-3-yl-methyl)-acrylic acid ethyl ester
• 英文别名: Ethyl 2-[hydroxy(thiophen-3-yl)methyl]prop-2-enoate
• CAS: 652980-13-7
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: JHLPMGNUDGSWGB-UHFFFAOYSA-N

物化性质

• 沸点：
  344.2±42.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯乙酮肟 、 2-(Hydroxy-thiophen-3-yl-methyl)-acrylic acid ethyl ester 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以65%的产率得到3-Hydroxy-2-[1-phenyl-eth-(E)-ylideneaminooxymethyl]-3-thiophen-3-yl-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Novel Oxime Functionalized Aldol Products via Michael Addition of Oximes Onto Baylis–Hillman Adducts

  摘要：

  Triphenylphosphine-catalyzed Michael addition of oximes 2 onto Baylis-Hillman (B-H) adducts 1 led to an easy access to a novel class of oxime functionalized aldol products 3. This demonstrates the first use of an oxygen-centered nucleophile in Michael addition to B-H adducts, without touching any other functional group. Deprotection of oxime in 3 was further demonstrated using molecular hydrogen (1 atm) and 10% Pd/C (cat.) to furnish functionalized 1,3-diols 4 as potentially useful synthons with optional backbone choice (R 3 and EWG).

  DOI：

  10.1080/00397910500334132
• 作为产物：
  描述：

  3-噻吩甲醛 、 丙烯酸乙酯 在 三乙烯二胺 作用下， 反应 16.0h， 以60%的产率得到2-(Hydroxy-thiophen-3-yl-methyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Porcine Liver Esterase Catalyzed Kinetic Resolution of Baylis-Hillman (B-H) Adducts

  摘要：

  Esterase from porcine liver smoothly resolves varieties of racemic 2-methylene-3-substituted-3-hydroxypropanoates (B-H adducts) to obtain the corresponding unreacted esters in very good to excellent ee (94 to >99%, seven examples) and hydrolyzed acids in good ee (58-75%). Substitution in B-H adducts, chosen for resolution, are funtionalized phenyl, thiophen-3-yl, cinnamyl, and alkyl groups.

  DOI：

  10.1081/scc-120025180

文献信息

• Synthesis of α-methylene-δ-oxo-γ-amino esters via Rh(<scp>ii</scp>)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita–Baylis–Hillman adducts
  作者：Hyun Ji Jeon、Mi Soo Kwak、Da Jung Jung、Jean Bouffard、Sang-gi Lee

  DOI：10.1039/c6ob02086k

  日期：——

  1-alkynes and sulfonyl azides, with Morita–Baylis–Hillman (MBH) adducts afforded highly functionalized α-methylene-δ-oxo-γ-amino esters in excellent yields with broad functional group tolerance. This transformation can also be successfully accomplished as a multicomponent all-in-one-pot reaction of 1-alkynes, sulfonyl azides and MBH adducts in the presence of Cu(I) and Rh(II) catalysts.

  铑（Ⅱ）催化的1-磺酰基-1,2,3-三唑（由1-炔烃和磺酰叠氮化物制备）与森田-贝利斯-希尔曼（MBH）加合物的偶联提供了高度官能化的α-亚甲基-δ-氧代-γ-氨基酯，收率高，具有宽泛的官能团耐受性。这种转化也可以在Cu（I）和Rh（II）催化剂存在下，通过1-炔烃，磺酰叠氮化物和MBH加合物的多组分一锅法成功完成。
• Synthesis of Novel Oxime Functionalized Aldol Products via Michael Addition of Oximes Onto Baylis–Hillman Adducts
  作者：Debnath Bhuniya、Srinivas Gujjary、Sujata Sengupta

  DOI：10.1080/00397910500334132

  日期：2006.2.1

  Triphenylphosphine-catalyzed Michael addition of oximes 2 onto Baylis-Hillman (B-H) adducts 1 led to an easy access to a novel class of oxime functionalized aldol products 3. This demonstrates the first use of an oxygen-centered nucleophile in Michael addition to B-H adducts, without touching any other functional group. Deprotection of oxime in 3 was further demonstrated using molecular hydrogen (1 atm) and 10% Pd/C (cat.) to furnish functionalized 1,3-diols 4 as potentially useful synthons with optional backbone choice (R 3 and EWG).
• Porcine Liver Esterase Catalyzed Kinetic Resolution of Baylis-Hillman (B-H) Adducts
  作者：Debnath Bhuniya、Sanju Narayanan、Taranpreet Singh Lamba、K. V. S. R. Krishna Reddy

  DOI：10.1081/scc-120025180

  日期：2003.11

  Esterase from porcine liver smoothly resolves varieties of racemic 2-methylene-3-substituted-3-hydroxypropanoates (B-H adducts) to obtain the corresponding unreacted esters in very good to excellent ee (94 to >99%, seven examples) and hydrolyzed acids in good ee (58-75%). Substitution in B-H adducts, chosen for resolution, are funtionalized phenyl, thiophen-3-yl, cinnamyl, and alkyl groups.