benzyl 2-benzylacrylate | 95176-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-benzylacrylate
• 英文别名: phenylmethyl α-methylenebenzenepropanoate；benzyl 2-benzylprop-2-enoate
• CAS: 95176-68-4
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: ILYJSOSRVQNFMO-UHFFFAOYSA-N

物化性质

• 沸点：
  377.5±21.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 2-benzylacrylate 在 10percentPd/C 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 21.0h， 生成 2-[[(2-carboxy-3-phenylpropyl)hydroxyphosphinyl]-methyl]pentanedioic acid
  参考文献：
  名称：

  Design and Pharmacological Activity of Phosphinic Acid Based NAALADase Inhibitors

  摘要：

  A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive mc del of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.

  DOI：

  10.1021/jm0001774
• 作为产物：
  描述：

  苄基丙二酸 在 potassium carbonate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 benzyl 2-benzylacrylate
  参考文献：
  名称：

  Design and Pharmacological Activity of Phosphinic Acid Based NAALADase Inhibitors

  摘要：

  A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive mc del of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.

  DOI：

  10.1021/jm0001774

文献信息

• Visible-light-promoted photocatalyst- and additive-free intermolecular trifluoromethyl-thio(seleno)cyanation of alkenes
  作者：Maheshwara Reddy Nadiveedhi、Suresh Reddy Cirandur、Srirama Murthy Akondi

  DOI：10.1039/d0gc01726d

  日期：——

  Photocatalyst- and additive-free trifluoromethyl-thio(seleno)cyanation of alkenes using visible light as the sole promoter is reported.

  无需光催化剂和添加剂，利用可见光作为唯一的促进剂，报道了烯烃的三氟甲硫(硒)氰化反应。
• High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction
  作者：Dhevalapally B. Ramachary、Chintalapudi Venkaiah、Y. Vijayendar Reddy

  DOI：10.1039/c4ob00667d

  日期：——

  A general process for the high-yielding synthesis of substituted chiral and achiral α-substituted acrylates was achieved through the sequential one-pot combination of a metal-free reductive coupling reaction followed by an Eschenmoser methylenation. The proline catalyzed reaction of Meldrum's acid, aldehydes and Hantzsch ester followed by methylenation was successful with Eschenmoser's salt in the

  通过无金属还原偶联反应的顺序一锅法结合然后进行Eschenmoser甲基化，可以实现高产率合成取代的手性和非手性α-取代的丙烯酸酯的一般方法。在醇溶剂存在下，Eschenmoser盐能成功地使脯氨酸催化Meldrum的酸，醛和Hantzsch酯的甲基化反应。本文中，我们显示了由手性/非手性α-取代丙烯酸酯高特权合成的合成原料，并显示它们是药物和天然产物合成中非常好的中间体。
• Renin inhibitors containing a pyridyl amino diol derived C-terminus
  作者：Holger Heitsch、Rainer Henning、Heinz Werner Kleemann、Wolfgang Linz、Wolf Ulrich Nickel、Dieter Ruppert、Hansjoerg Urbach、Adalbert Wagner

  DOI：10.1021/jm00071a009

  日期：1993.9

  the concept of transition-state analogs, a series of nonpeptide renin inhibitors with the new (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexane moiety at the C-terminal functionality were synthesized and evaluated for inhibition of renin both in vitro and in vivo. All compounds exhibited potencies in the nanomolar or even subnanomolar range when tested versus human renin in vitro. Selected

  基于过渡态类似物的概念，一系列具有新的（2S，3R，4S）-2-氨基-1-环己基-3,4-二羟基-6-（2-吡啶基）己烷部分的非肽肾素抑制剂合成了在C-末端的C末端功能，并在体外和体内评估了对肾素的抑制。当与人肾素进行体外测试时，所有化合物均显示出纳摩尔或什至亚纳摩尔范围的效力。在麻醉的，钠缺乏的恒河猴中评估选定的抑制剂，并在十二指肠内给予2 mg / kg的剂量后，平均动脉血压（MAP）明显降低。含有氨基哌啶基琥珀酸衍生的N端的化合物38（S 2864）是该系列中最有希望的成员。38种抑制人肾素的IC50为0.38 nM，不影响其他人天冬氨酸蛋白酶，
• Nickel-Catalyzed Arylation of C(sp³)–O Bonds in Allylic Alkyl Ethers with Organoboron Compounds
  作者：Xiaowei Li、Yuxiu Li、Zhong Zhang、Xiaolin Shi、Ruihua Liu、Zemin Wang、Xiangqian Li、Dayong Shi

  DOI：10.1021/acs.orglett.1c01879

  日期：2021.9.3

  A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale

  描述了镍催化的烯丙基烷基醚与有机硼化合物通过惰性 C(sp 3 )-O(烷基) 键断裂的交叉偶联。几种类型的烯丙基烷基醚可以与各种硼酸或其衍生物偶联，得到相应的产品，收率良好，具有广泛的官能团耐受性和出色的区域选择性。生物活性化合物的克级反应和后期修饰进一步证明了这种合成方法的实用性。
• Renin-inhibiting functionalized peptidyl aminodiols and - triols
  申请人：ABBOTT LABORATORIES

  公开号：EP0341602A2

  公开（公告）日：1989-11-15

  A renin inhibiting compound of the formula: or a pharmaceutically acceptable salt, ester or prodrug thereof.

  一个公式为的抑制肾素的化合物： 或其药用可接受的盐、酯或前药。