己酸,3-羟基-2-亚甲基-,甲基酯 | 18020-64-9

• 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
• 中文名称: 己酸,3-羟基-2-亚甲基-,甲基酯
• 英文名称: methyl 3-hydroxy-2-methylenehexanoate
• 英文别名: 3-Hydroxy-2-methylenehexanoic acid methyl ester；methyl 3-hydroxy-2-methylidenehexanoate
• CAS: 18020-64-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: YMHOPFPBSLGXDP-UHFFFAOYSA-N

物化性质

• 沸点：
  77-78 °C(Press: 5 Torr)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  己酸,3-羟基-2-亚甲基-,甲基酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 22.33h， 生成 2-甲基己-2-烯-1-醇
  参考文献：
  名称：

  Total Synthesis and Structure Determination of JBIR-108—A 2-Hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4

  摘要：

  The planar and stereostructures of JBIR-108 isolated from Streptomyces gramineus IR087Pi-4 were determined partly by spectral analysis, and these structural assignments were confirmed and completed by the total synthesis of both 1-epimers. The key stereocenters in JBIR-108 were constructed via a Corey-Bakshi-Shibata (CBS) reduction (C-1), vinylogous Mukaiyama aldol reaction (C-7), and Brown crotylation (C-14 and C-15). Although it was difficult to determine the stereochemistries at the C-1 and C-7 positions in the natural product using the modified Moshers method, the synthesis of two possible C-1 diastereomers enabled the identification of the configurations at the hitherto unknown stereocenters.

  DOI：

  10.1021/jo502198y
• 作为产物：
  描述：

  Methyl 3-hydroxy-2-methyl-2-(phenylthio)hexanoate 在 sodium periodate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 26.0h， 生成 己酸,3-羟基-2-亚甲基-,甲基酯
  参考文献：
  名称：

  向α-（1-羟烷基）-和α-（1-烷氧基-烷基）-α，β-不饱和酯中添加溴

  摘要：

  电子贫烯烃，2-（1-羟烷基）-和2-（1-烷氧基烷基）丙酸酯，2b-d和（E）-2-（1-羟乙基）-2-丁烯酸甲酯的常规离子溴化3a，收益率高于80％。用两当量的强碱处理（E）-3-溴-2- [1-[（2-甲氧基乙氧基）甲氧基]丁基]丙酸16，反应可能与羟基双溴化物和溴代贝克莱德合成有关，可能通过生成二价阴离子19进行卤素-金属交换反应，得到丙烯酸18。

  DOI：

  10.1016/s0040-4020(01)89031-1

文献信息

• Diastereoselective synthesis of α-(aminomethyl)-γ-butyrolactones via a catalyst-free aminolactonization
  作者：P. Veeraraghavan Ramachandran、Daniel R. Nicponski

  DOI：10.1039/c4cc05765a

  日期：——

  An auto-catalytic domino reaction involving an aza-Michael reaction, proton transfer, and lactonization furnishing α-aminomethyl-γ-butyrolactones in near quantitative yields and excellent diastereoselectivity is described.

  一种涉及aza-Michael反应、质子转移和内酯化的自催化多米诺反应，以近定量的收率和优秀的对映选择性提供了α-氨基甲基-γ-丁内酯。

• 4-(Dimethylamino)pyridine as a catalyst for the lactonization of 4-hydroxy-2-methylenebutanoate esters
  作者：Daniel R. Nicponski

  DOI：10.1016/j.tetlet.2014.02.024

  日期：2014.3

  The catalytic action of 4-(dimethylamino)pyridine (DMAP) in lactonizing 4-hydroxy-2-methylenebutanoate esters to 2-methylene-γ-butyrolactones is described. The use of DMAP, which functions as an excellent complement to the more traditional acid-catalyzed lactonization protocol, allows for the synthesis of 2-methylene-γ-butyrolactones containing acid-sensitive groups under essentially neutral conditions

  描述了4-（二甲基氨基）吡啶（DMAP）在将4-羟基-2-亚甲基丁酸酯酯化为2-亚甲基-γ-丁内酯中的催化作用。DMAP的使用可作为对更传统的酸催化内酯化方法的出色补充，可以在基本上中性的条件下合成含有酸敏感基团的2-亚甲基-γ-丁内酯。
• Tandem conjugate addition-aldol reaction to α,β-unsaturated esters and ketones using titanium amide
  作者：Akira Hosomi、Toshiharu Yanagi、Makoto Hojo

  DOI：10.1016/s0040-4039(00)79926-6

  日期：1991.5

  Titanium dialkylamide, readily available, adds to a α,β-unsaturated esters and ketones in a conjugate addition mode to give ester and ketone enolates, respectively, which are successively quenched with electrophiles such as aldehydes and acetals. The aldol products can be readily converted to the corresponding deaminated or dehydrated derivatives selectively.

  容易获得的二烷基酰胺钛以共轭加成方式加到α，β-不饱和酯和酮上，分别得到酯和酮烯酸酯，然后用亲电子试剂如醛和缩醛将其连续淬灭。羟醛产物可以容易地选择性地转化为相应的脱氨基或脱水衍生物。
• The C–OH/P–H dehydrative cross-coupling for the construction of the P–C bond under metal-free conditions
  作者：Peizhong Xie、Jinyu Wang、Jing Fan、Yanan Liu、Xiangyang Wo、Teck-Peng Loh

  DOI：10.1039/c7gc00882a

  日期：——

  Herein, we report an atom-economical and environmentally benign approach for P–C bond construction via C–OH/P–H dehydrative cross-coupling reaction. This reaction was carried out under metal-free conditions, proceeds in the absence of any solvent and delivered allylic phosphorus compounds in high yields with wide functional group tolerance.

  在本文中，我们报告了通过C-OH / P-H脱水交叉偶联反应进行P-C键结构的一种原子经济且对环境无害的方法。该反应在无金属的条件下进行，在没有任何溶剂的情况下进行，并以高收率和宽的官能团耐受性递送烯丙基磷化合物。
• 1,1′-Carbonyldiimidazole mediates the synthesis of N-substituted imidazole derivatives from Morita–Baylis–Hillman adducts
  作者：Manoel T. Rodrigues、Marilia S. Santos、Hugo Santos、Fernando Coelho

  DOI：10.1016/j.tetlet.2013.10.146

  日期：2014.1

  straightforward method for the synthesis of N-substituted imidazole derivatives. 1,1-carbonyldiimidazole mediates the process, which requires no activation group step. We obtained imidazole derivatives in high yields and with short reaction times. To demonstrate the synthetic significance of the aforementioned compounds, we also describe the synthesis of novel ionic liquids from these derivatives.

  在这封信中，我们描述了一种简单而直接的合成N-取代的咪唑衍生物的方法。1,1-羰基二咪唑介导了该过程，该过程不需要活化基团步骤。我们以高收率和短反应时间获得了咪唑衍生物。为了证明上述化合物的合成意义，我们还描述了由这些衍生物合成新型离子液体的方法。