| 1316313-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1316313-13-9
• 化学式: C₁₇H₁₉F₃O₅
• 分子量: 360.33
• InChiKey: MRHLURIAAAPSJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 calcium fluoride 、 水 、 hydroquinidine (anthraquinone-1,4-diyl) diether 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 72.0h， 以88%的产率得到(S)-(+)-methyl 3-hydroxy-2-methylene-3-(3-trifluoromethylphenyl)propanoate
  参考文献：
  名称：

  Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita–Baylis–Hillman Carbonates with Water

  摘要：

  A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using O-18-labeling experiments.

  DOI：

  10.1021/jo201096e
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 在 三乙烯二胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  膦催化的[3 + 2]森田-贝利斯-希尔曼碳酸盐与异恶唑基烯烃的环化

  摘要：

  已开发出一种膦催化的森田-贝利斯-希尔曼（MBH）碳酸酯与3-甲基-4-硝基-5-苯乙烯基恶唑的碳酸盐环化反应[3 + 2]，以中等至良好的产率提供各种多功能异恶唑，具有中等至优异的非对映选择性。用螺环手性膦作为催化剂，获得高达89％的ee。

  DOI：

  10.1021/acs.joc.0c01948

文献信息

• Phosphine-Catalyzed Highly Enantioselective [3 + 3] Cycloaddition of Morita–Baylis–Hillman Carbonates with C,N-Cyclic Azomethine Imines
  作者：Lei Zhang、Honglei Liu、Guanyu Qiao、Zhanfeng Hou、Yang Liu、Yumei Xiao、Hongchao Guo

  DOI：10.1021/jacs.5b01138

  日期：2015.4.8

  The first phosphine-catalyzed highly enantioselective [3 + 3] cycloaddition of Morita-Baylis-Hillman carbonates with C,N-cyclic azomethine imines is described. Using a spirocyclic chiral phosphine as the catalyst, a novel class of pharmaceutically interesting 4,6,7,11b-tetrahydro-1H-pyridazino[6,1-a]iso-quinoline derivatives were obtained in high yields with good to excellent diastereoselectivities

  描述了第一个膦催化的 Morita-Baylis-Hillman 碳酸酯与 C,N-环状偶氮甲亚胺的高度对映选择性 [3 + 3] 环加成反应。使用螺环手性膦作为催化剂，以高产率获得了一类新的具有药学意义的 4,6,7,11b-四氢-1H-哒嗪并[6,1-a]异喹啉衍生物，具有良好到优异的非对映选择性和极其出色的对映选择性 (98->99% ee)。
• Enantioselective Synthesis of Quinazoline-Based Heterocycles through Phosphine-Catalyzed Asymmetric [3+3] Annulation of Morita−Baylis−Hillman Carbonates with Azomethine Imines
  作者：Leijie Zhou、Chunhao Yuan、Cheng Zhang、Lei Zhang、Zhenzhen Gao、Chang Wang、Honglei Liu、Yang Wu、Hongchao Guo

  DOI：10.1002/adsc.201601434

  日期：2017.7.3

  Enantioselective synthesis of chiral quinazoline‐based heterocycles is achieved through a chiral phosphine‐catalyzed [3+3] annulation reaction of quinazoline‐based 1,3‐dipoles with Morita−Baylis−Hillman carbonates. The reaction proceeds smoothly under mild conditions to give various chiral heterocyclic compounds in high yields with excellent diastereoselectivities and enantioselectivities. Further

  手性喹唑啉基杂环的对映选择性合成是通过手性膦催化的喹唑啉基1,3-偶极与Morita-Baylis-Hillman碳酸盐的手性[3 + 3]环化反应而实现的。反应在温和条件下平稳进行，以高收率得到各种手性杂环化合物，并具有优异的非对映选择性和对映选择性。环化产物的进一步不同的精制工作很好地产生了新的四氢喹唑啉衍生物。
• Chiral Phosphine-Catalyzed Enantioselective [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Cyclic 1-Azadienes: Synthesis of Functionalized Cyclopentenes
  作者：Yang Wu、Yang Liu、Wenjun Yang、Honglei Liu、Leijie Zhou、Zhanhu Sun、Hongchao Guo

  DOI：10.1002/adsc.201600607

  日期：2016.11.17

  catalyst, the asymmetric [3+2] annulation of Morita–Baylis–Hillman carbonates with cyclic 1‐azadienes proceeded smoothly under mild conditions to give various enantiomerically enriched cyclopentene derivatives bearing three consecutive tertiary stereocenters and a sulfamate moiety in moderate to excellent yields with moderate to excellent enantioselectivities and excellent diastereoselectivities.

  使用双官能手性膦作为催化剂，森田-贝利斯-希尔曼碳酸盐与环状1-氮杂二烯的不对称[3 + 2]环化在温和条件下顺利进行，得到了具有三个连续的三级立体中心的各种对映体富集的环戊烯衍生物。氨基磺酸盐部分，具有中等至优异的收率，具有中等至优异的对映选择性和出色的非对映选择性。
• Direct Asymmetric Allylic Alkenylation of <i>N</i>-Itaconimides with Morita–Baylis–Hillman Carbonates
  作者：Wenguo Yang、Davin Tan、Lixin Li、Zhiqiang Han、Lin Yan、Kuo-Wei Huang、Choon-Hong Tan、Zhiyong Jiang

  DOI：10.1021/jo3012539

  日期：2012.8.3

  asymmetric allylic alkenylation of Morita–Baylis–Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity

  使用市售的金鸡纳生物碱催化剂，已经开发出以N- itaconimides作为亲核试剂的Morita-Baylis-Hillman（MBH）碳酸酯的不对称烯丙基烯基化反应。以中等至优异的产率（高达99％）和良好至优异的对映选择性（高达91％ee）获得了多种多功能手性α-亚甲基-β-马来酰亚胺酯。区域选择性和立体选择性的起源已通过DFT方法进行了验证。计算得到的各种过渡态的几何形状和相对能量，有力地支持了所观察到的区域和对映选择性。
• Palladium-Catalyzed Alkynylation of Morita–Baylis–Hillman Carbonates with (Triisopropylsilyl)acetylene on Water
  作者：Yangxiong Li、Li Liu、Delong Kong、Dong Wang、Weichun Feng、Tao Yue、Chaojun Li

  DOI：10.1021/acs.joc.5b00728

  日期：2015.6.19

  Direct alkynylation of Morita–Baylis–Hillman carbonates with (triisopropylsilyl)acetylene catalyzed by a Pd(OAc)2–NHC complex was developed “on water” to give the corresponding 1,4-enynes. The significant effects of water amount in the solvent on further transformations of 1,4-enynes were investigated.

  由Pd（OAc）2 -NHC络合物催化的森田-贝利斯-希尔曼碳酸盐与（三异丙基甲硅烷基）乙炔的直接烷基化反应在水上生成相应的1,4-炔烃。研究了溶剂中水量对1,4-炔烃进一步转化的显着影响。