1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol | 194156-04-2

• 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: 1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol
• 英文别名: 1-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-en-1-ol
• CAS: 194156-04-2
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: ZJRWETIMDZVOLM-UHFFFAOYSA-N

物化性质

• 沸点：
  316.4±30.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1'-羟基草蒿脑
  参考文献：
  名称：

  Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  摘要：

  1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 mu M. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1'-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2'-3' double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1'- and 2'-positions reduced the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.070
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol
  参考文献：
  名称：

  脂肪酶催化的旋光性1'-乙酰氧基甲氧乙酸乙酸酯的制备及其与人白血病HL-60细胞凋亡活性的结构-活性关系。

  摘要：

  使用旋光性ACA和各种外消旋ACA类似物研究了1'-乙酰氧基甲氧乙酸乙酸酯（ACA）对人白血病HL-60细胞凋亡活性的结构-活性关系。天然型（或带有不同酰基的）ACA具有较高的凋亡活性，但邻位或间位异构体，4-脱乙酰氧基类似物和2'-3'脱氢衍生物没有作用，或活性较弱。通过脂肪酶催化的酯化反应制备旋光的（R）-和（S）-ACA。在回流温度下使用乙酸乙烯酯-四氢呋喃的混合物（1：1v / v）作为溶剂，获得光学纯的（R）-和（S）-ACA（分别为99.7％ee和99.1％ee）。通过MTT分析和检测典型的凋亡现象（DNA片段化，caspase-3激活和PARP裂解）和这两个活性几乎相等。这些结果表明，ACA对HL-60细胞具有凋亡活性的基本部分是4-乙酰氧基和C-2'和C-3'之间的不饱和双键的存在，以及在1处的构型。 '-位置与活动无关。

  DOI：

  10.1016/j.bmc.2005.10.029

文献信息

• Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode
  作者：Lorenzo Lombardi、Daniele Bellini、Andrea Bottoni、Matteo Calvaresi、Magda Monari、Alessandro Kovtun、Vincenzo Palermo、Manuela Melucci、Marco Bandini

  DOI：10.1002/chem.202001373

  日期：2020.8.17

  The site‐selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt % loading) as the promoter. Metal‐free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 %) and excellent site‐ and

  在碳催化作用下，在氧化石墨烯（GO，10 wt％负载）作为促进剂的情况下，用醇对吲哚进行位点选择性烯丙基和烯丙基脱芳香化反应。无金属的条件，无化学计量的添加剂，环境友好的条件（H 2 O / CH 3 CN，55°C，6 h），广泛的底物范围（33个实例，产率高达92％）以及出色的定点和立体选择性目前的方法。此外，GO功能发挥的共价激活模型得到了光谱，实验和计算证据的证实。还记录了通过简单的酸性处理来回收和再生GO催化剂。
• [EN] ANTIDIABETIC BICYCLIC COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES ANTIDIABÉTIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2016022742A1

  公开（公告）日：2016-02-11

  Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

  结构式（I）的新化合物及其药用盐是G蛋白偶联受体40（GPR40）的激动剂，可能对通过G蛋白偶联受体40介导的疾病的治疗、预防和抑制具有用处。本发明的化合物可能对2型糖尿病的治疗有用，以及对常与该疾病相关的疾病，包括肥胖和脂质紊乱，如混合型或糖尿病性脂质代谢异常、高脂血症、高胆固醇血症和高甘油三酯血症的治疗有用。
• One-Flask Tethered Ring Closing Metathesis-Electrocyclic Ring Opening for the Highly Stereoselective Synthesis of Conjugated Z/E-Dienes
  作者：Bernd Schmidt、Oliver Kunz

  DOI：10.1002/ejoc.201101497

  日期：2012.2

  A one-flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base-mediated ring opening gives 2Z,4E-configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised.

  包括衍生自烯丙醇的丁烯酸酯的闭环复分解 (RCM) 和碱介导的开环的单瓶反应序列以高产率和立体选择性得到 2Z,4E 构型的二烯酸。该方法在天然产物 fusanolide A 的合成中的应用表明最初发表的结构被错误地分配，应该进行修改。
• Asymmetric Allylic Alkylation of β-Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst
  作者：Yusuke Kita、Rahul D. Kavthe、Hiroaki Oda、Kazushi Mashima

  DOI：10.1002/anie.201508757

  日期：2016.1.18

  Asymmetric allylic alkylation of β‐ketoesters with allylic alcohols catalyzed by [Ni(cod)2]/(S)‐H8‐BINAP was found to be a superior synthetic protocol for constructing quaternary chiral centers at the α‐position of β‐ketoesters. The reaction proceeded in high yield and with high enantioselectivity using various β‐ketoesters and allylic alcohols, without any additional activators. The versatility of

  发现[Ni（cod）2 ] /（S）-H 8 -BINAP催化的烯丙基醇与β-酮酯的不对称烯丙基烷基化是在β-酮酯的α-位上构建季手性中心的优良合成方案。使用各种β-酮酸酯和烯丙基醇，无需任何其他活化剂，即可以高收率和高对映选择性进行反应。展示了这种方法在获取有用和对映体富集产品方面的多功能性。
• Cross metathesis of allyl alcohols: how to suppress and how to promote double bond isomerization
  作者：Bernd Schmidt、Sylvia Hauke

  DOI：10.1039/c3ob40167g

  日期：——

  formation of ketones, resulting from uncontrolled and undesired double bond isomerization. By conducting the CM in the presence of phenol, the catalyst loading and the reaction time required for quantiative conversion can be reduced, and isomerization can be suppressed. On the other hand, consecutive isomerization can be deliberately promoted by evaporating excess methyl acrylate after completing cross

  在标准条件下，烯丙醇和 丙烯酸甲酯伴随着由于不受控制和不希望的双键异构化导致的酮的形成。通过在以下人员在场的情况下执行CM苯酚，可以减少定量转化所需的催化剂载量和反应时间，并且可以抑制异构化。另一方面，通过过量蒸发可以有意地促进连续的异构化。丙烯酸甲酯 完成交叉复分解后，并添加碱或硅烷作为化学触发剂。