(E)-ethoxystyrene | 20565-86-0

• 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: (E)-ethoxystyrene
• 英文别名: (E)-(2-ethoxyvinyl)benzene；β-ethoxystyrene；[(E)-2-ethoxyethenyl]benzene
• CAS: 20565-86-0
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: FZHNODDFDJBMAS-CMDGGOBGSA-N

物化性质

• 熔点：
  106.5-107.0 °C
• 沸点：
  98-99 °C(Press: 10 Torr)
• 密度：
  0.966±0.06 g/cm3(Predicted)
• 保留指数：
  1214

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-ethoxystyrene 在 platinum(IV) oxide 二异丙氧基二氯化钛 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.75h， 生成 trans-3,4-diphenyl-N-(p-tolylsulfonyl)pyrrolidine
  参考文献：
  名称：

  Nitroalkene [4+2] cycloaddition as a general and stereoselective route to the synthesis of 3,3- and 3,4-disubstituted pyrrolidines

  摘要：

  2,2-Disubstituted 1-nitroalkenes 12 undergo Lewis acid-promoted [4 + 2] cycloadditions with n-butyl vinyl ether to afford cyclic nitronates 14 as anomeric mixtures in good yields. The resulting nitronates were reduced with hydrogen in the presence of Adam's catalyst to afford 3,3-disubstituted pyrrolidines which were isolated in good yield as their N-p-toluenesulfonamides 17. Cycloadditions of (E)-2-nitrostyrene with ethyl (E)- and (Z)-1-propenyl ethers provided for the stereoselective synthesis of cis- and trans-3-phenyl-4-methyl-N-(p-tolylsulfonyl)pyrrolidine. Similarly, trans-3,4-diphenyl-N-(p-tolysulfonyl)pyrrolidine was prepared from (E)-2-nitrostyrene and ethyl (E)-2-styryl ether.

  DOI：

  10.1021/jo00067a017
• 作为产物：
  描述：

  2-溴-2-苯基乙醛二乙缩醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以83%的产率得到(E)-ethoxystyrene
  参考文献：
  名称：

  实用的（E）-烯醇醚的区域选择性合成方法

  摘要：

  报道了一种新的实用且高度区域选择性的（E）-烯醇醚合成方法。（É）烯醇醚类（Ë：ž = 93：7-99：1）从相应的烯醇乙酸酯（其制备ê：ž在两个步骤由溴化和经由金属α-bromodialkylacetal的抗消除：≅31）卤素交换。

  DOI：

  10.1016/s0040-4039(00)00603-1

文献信息

• Synthesis of Piperidine Derivatives by Rhodium- Catalyzed Tandem Reaction of<i>N</i>-Sulfonyl-1,2,3-Triazole and Vinyl Ether
  作者：Sisi Yu、Yuehui An、Wenlin Wang、Ze-Feng Xu、Chuan-Ying Li

  DOI：10.1002/adsc.201800191

  日期：2018.6.5

  A chemoselective tandem reaction of 4‐acyloxymethylene‐1‐sulfonyl‐1,2,3‐triazole and vinyl ether was reported, producing polysubstituted piperidine derivatives in up to 96% yield. The key intermediate N‐sulfonyl 1‐azadiene generated by migration of the OAc group to the α‐imino rhodium carbene was isolated and a plausible mechanism was proposed. Several related ring systems were constructed from the

  据报道，4-酰氧基亚甲基-1-磺酰基-1,2,3-三唑与乙烯基醚发生化学选择性串联反应，产生多取代哌啶衍生物，收率高达96％。分离了由OAc基团迁移至α-亚氨基铑卡宾而生成的关键中间体N-磺酰基1-氮杂二烯，并提出了一个合理的机理。从高度功能化的产品构建了几个相关的环系统。
• Interrogating Pd(II) Anion Metathesis Using a Bifunctional Chemical Probe: A Transmetalation Switch
  作者：John J. Molloy、Ciaran P. Seath、Matthew J. West、Calum McLaughlin、Neal J. Fazakerley、Alan R. Kennedy、David J. Nelson、Allan J. B. Watson

  DOI：10.1021/jacs.7b11180

  日期：2018.1.10

  Ligand metathesis of Pd(II) complexes is mechanistically essential for cross-coupling. We present a study of halide→OH anion metathesis of (Ar)PdII complexes using vinylBPin as a bifunctional chemical probe with Pd(II)-dependent cross-coupling pathways. We identify the variables that profoundly impact this event and allow control to be leveraged. This then allows control of cross-coupling pathways

  Pd(II) 配合物的配体复分解对于交叉偶联在机械上是必不可少的。我们使用vinylBPin作为具有Pd（II）依赖性交叉偶联途径的双功能化学探针，对（Ar）PdII复合物的卤化物→OH阴离子复分解进行了研究。我们确定了对这一事件产生深远影响的变量，并允许利用控制权。然后，这允许通过促进或抑制有机硼金属转移来控制交叉偶联途径，从而产生 Suzuki-Miyaura 或 Mizoroki-Heck 产品。我们展示了这种金属转移开关如何用于级联交叉偶联/Diels-Alder 反应中的合成增益，提供硼酸化或非硼酸化碳环，包括类固醇类支架。
• Nickel- or palladium-catalyzed cross coupling. 31. Palladium- or nickel-catalyzed reactions of alkenylmetals with unsaturated organic halides as a selective route to arylated alkenes and conjugated dienes: scope, limitations, and mechanism
  作者：Eiichi Negishi、Tamotsu Takahashi、Shigeru Baba、David E. Van Horn、Nobuhisa Okukado

  DOI：10.1021/ja00242a024

  日期：1987.4

  Al, Zr, and Zn were 2, 3, and > 2000 mmol of (E)-1-octenylbenzene (8) per mmol of Pd(PPh/sub 3/)/sub 4/ per hour at room temperature, respectively. The stoichiometric reaction of PhPd(PPh/sub 3/)/sub 2/I (6) with 1.2 equiv of (E)-1-octenylzinc chloride (7) in a 2:1 mixture of CD/sub 2/Cl/sub 2/ and THF was examined in detail. The reaction follows second-order kinetics (k/sub 2/ = 2.9 L/(mol.min) at

  含有 Al、Zr 和 Zn 的立体和区域定义的烯基金属与芳基和烯基碘化物和溴化物在催化量的含有膦配体（如 PPh/sub 3/）的 Pd 或 Ni 配合物存在下反应，得到相应的交叉偶联产品。钯催化剂在烯基-芳基和烯基-烯基偶联反应中允许近 100% 的立体定向，而镍催化剂导致烯基-烯基偶联中的部分立体化学混乱。尽管还使用了许多其他金属，包括 Li、Mg、Cd、Hg、B、Si、Sn、Ti 和 Ce，但在本研究中使用的条件下，结果不如使用 Al、Zr 和 Zn 获得的结果。PhI 与 (E)-1-辛烯基金属（包含 Al、Zr 和 Zn）的钯催化反应的转换数为 2、3 和 > 在室温下，每小时每毫摩尔 Pd(PPh/sub 3/)/sub 4/ 分别为 2000 毫摩尔 (E)-1-辛烯基苯 (8)。PhPd(PPh/sub 3/)/sub 2/I (6) 与 1.2 当量 (E)-1-辛烯基氯化锌
• A PROCESS FOR PREPARING FUNCTIONAL POLYMERS THROUGH ADDITION OF AMINO AND POLYMERYL GROUPS TO ALDEHYDE MOIETIES
  申请人：Dow Global Technologies LLC

  公开号：US20180273654A1

  公开（公告）日：2018-09-27

  The present disclosure relates to a one-pot process for synthesizing functional compounds or functional polymers by reacting an aldehyde with an alkyl-zinc or polymeryl-zinc composition in the presence of a specific Lewis acid, wherein the reaction is rapid and facile at high temperatures.

  本公开涉及一种一锅法合成功能化合物或功能聚合物的方法，通过在特定Lewis酸存在下，将醛与烷基锌或聚合锌组合物反应，反应在高温下迅速且容易进行。
• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES, À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2011015241A1

  公开（公告）日：2011-02-10

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT2B (5-HT2B receptor), and on the prostaglandin F2 • receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

  构象受限、空间定义的12-30元大环环系统(I型)由三个不同的构建模块组成：芳香模板a、构象调节剂b和间隔基团c，详细描述在说明书和专利要求中。I型大环可通过并行合成或组合化学方法轻松制备。它们设计用于与特定生物靶点相互作用。特别是，它们在胃动素受体(MR受体)、5-羟色胺受体亚型5-HT2B(5-HT2B受体)和前列腺素F2•受体(FP受体)上显示激动或拮抗活性。因此，它们潜在用于治疗胃肠道低动力障碍，如糖尿病性胃轻瘫和便秘型肠易激综合征；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；眼压增高，如青光眼和早产。