(1E,3E)-4-(2-chlorophenyl)-1-phenyl-1,3-butadiene | 69286-52-8

• 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: (1E,3E)-4-(2-chlorophenyl)-1-phenyl-1,3-butadiene
• 英文别名: 1-chloro-2-((3E)-4-phenylbuta-1,3-dien-1-yl)benzene；1-chloro-2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)benzene；1-Phenyl-4-(2'-chlorphenyl)-buta-1,3-dien；1t-(2-chloro-phenyl)-4t-phenyl-buta-1,3-diene；trans-trans-4-Phenyl-1-(2-chlor-phenyl)-butadien-(1.3)；1t-(2-Chlor-phenyl)-4t-phenyl-buta-1,3-dien；1-chloro-2-[(1E,3E)-4-phenylbuta-1,3-dienyl]benzene
• CAS: 69286-52-8
• 化学式: C₁₆H₁₃Cl
• 分子量: 240.732
• InChiKey: XLHSIACSHBDRSU-ZVSIBQGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  马来酸酐 、 (1E,3E)-4-(2-chlorophenyl)-1-phenyl-1,3-butadiene 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Alcohol Drinkers Overreport Their Energy Intake in the BIRNH Study: Evaluation by 24-Hour Urinary Excretion of Cations

  摘要：

  Objective: Alcohol drinkers are generally considered to underreport their alcohol intake, but little is known about whether they correctly report their energy intake (EI). We assessed the validity of the reported energy intake of alcohol drinkers using the 24-hour urinary (U) excretion of potassium (K) and sodium (Na) as biomarkers.Methods: A total of 2,124 men and 1,998 women 25 to 74 years of age with a 24-hour urine collection. a random sample of the Belgian Interuniversity Research on Nutrition and Health (BIRNH), were studied. Dietary intake (D), including alcohol consumption, was assessed by a one-day food record, Basal metabolic rate (BMR) was predicted from age gender and weight. As a measure for the degree of reporting error. D-K/U-K, D-Na/U-Na, EI/U-K, Non-alcohol EI/U-Na (NAEI/U-Na), Ei/U-Na, EVU-creatinine and EI/BMR ratios were calculated and compared among non-, moderate and heavy drinkers in both genders.Results: El, NAEI and all seven ratios examined generally increased with the level of alcohol intake in both genders. After adjustment for age, body mass index, smoking and educational level, most ratios were significantly higher in moderate drinkers (p < 0.02 to p < 0.0001) and in heavy drinkers (all p < 0.0001) than in non-drinkers. These differences were most significant in male heavy drinkers. The exceptions were D-K/U-K. D-Na/U-Na and NAEI/U-Na in moderate and female heavy drinkers and EI/U-K in male moderate drinkers. The estimated amount of the overreporting of El by heavy drinkers was 27.8% in men and 13.7% in women.Conclusions: This study provides evidence that El and NAEI obtained from the BIRNH study was overreported among alcohol drinkers, especially among male heavy drinkers. It also indicates that El from alcohol replaced El from food.

  DOI：

  10.1080/07315724.2001.10719060
• 作为产物：
  描述：

  (E)-1-chloro-2-(4-phenylbut-3-en-1-yn-1-yl)benzene 在 乙醇 、 C₃₂H₄₀ClIrNP 、 叔丁胺 作用下， 反应 36.0h， 以98%的产率得到(1E,3E)-4-(2-chlorophenyl)-1-phenyl-1,3-butadiene
  参考文献：
  名称：

  铱催化选择性反式半氢化 1,3-烯炔与乙醇：获得 (E,E)-1,4-二芳基丁二烯

  摘要：

  使用新的 (PCN)Ir 配合物作为预催化剂和t BuNH 2作为助催化剂，开发了以乙醇为氢源的 1,3-烯炔的反式半氢化反应。该催化剂体系以高产率和立体选择性提供了一种高效且原子经济地获得不对称 ( E , E )-1,4-二芳基丁二烯的途径。监测过程显示，1,3-烯炔的三键顺式半氢化（形成 ( E , Z )-丁二烯）和 ( E , Z ) 到-( E , E ) 异构化形成( , _E )-丁二烯。

  DOI：

  10.1021/acs.orglett.2c02327

文献信息

• Palladium-Catalyzed Stereoselective Synthesis of (E)-Stilbenes via Organozinc Reagents and Carbonyl Compounds
  作者：Jin-Xian Wang、Kehu Wang、Lianbiao Zhao、Hongxia Li、Ying Fu、Yulai Hu

  DOI：10.1002/adsc.200606016

  日期：——

  In the presence of a catalytic amount of PdCl2(PPh3)2 and a silylating agent, organozinc halides reacted with carbonyl compounds to give the corresponding (E)-stilbenes in good to excellent yields under mild conditions. The reaction mechanism is briefly discussed.

  在催化量的PdCl 2（PPh 3）2和甲硅烷基化剂的存在下，有机锌卤化物与羰基化合物反应，在温和的条件下以良好或优异的收率得到相应的（E）-芪。简要讨论了反应机理。
• Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction
  作者：Yuki Yamamoto、Shin-ichi Kawaguchi、Misaki Nishimura、Yuki Sato、Yoshihisa Shimada、Akihiro Tabuchi、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1021/acs.joc.0c01926

  日期：2020.11.20

  phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity

  这项研究表明，可以在Wittig反应中使用适当的氟膦来回收磷源。由空气稳定的膦试剂合成了设计的氟膦，该磷膦在其磷原子和全氟烷基之间具有一个乙烯间隔基。合成的膦可用于Wittig反应过程，以足够的收率和立体选择性获得各种烯烃。使用氟双相体系从反应混合物中提取伴随形成的氟氧化膦。通过用二异丁基氢化铝还原氟代膦氧化物来再生氟代膦。最后，进行了一系列的克级磷回收过程，包括Wittig反应，分离，还原和再利用。
• A Highly Tunable Stereoselective Olefination of Semistabilized Triphenylphosphonium Ylides with <i>N</i>-Sulfonyl Imines
  作者：De-Jun Dong、Hai-Hua Li、Shi-Kai Tian

  DOI：10.1021/ja910238f

  日期：2010.4.14

  The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph(3)P horizontal lineCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly

  Wittig 反应涉及三苯基鏻叶立德（Ph(3)P 水平线 CHR）与醛的直接烯化反应可以说是最常用的烯烃合成方法，但通常它会产生 Z-和 E-烯烃的混合物，用于半稳定的三苯基鏻叶立德（R = 芳基或乙烯基）。我们开发了一种简单有效的方案，通过用 N-磺酰基亚胺代替 Wittig 反应中使用的醛，显着提高立体选择性，N-磺酰基亚胺相对于醛具有独特的电子和空间特性。广泛的芳香族、α、β-不饱和、和带有适当 N-磺酰基的脂肪族亚胺在温和的反应条件下与各种亚苄基三苯基正膦或烯丙基三苯基正膦平稳地进行烯化反应，以良好至极好的收率和大于 99:1 的立体选择性提供一系列共轭烯烃的 Z-和 E-异构体. 此外，该可调协议已成功应用于两种抗癌剂 DMU-212 及其 Z 异构体的高度立体选择性合成。
• US4250053A
  申请人：——

  公开号：US4250053A

  公开（公告）日：1981-02-10
• Alcohol Drinkers Overreport Their Energy Intake in the BIRNH Study: Evaluation by 24-Hour Urinary Excretion of Cations
  作者：Jianjun Zhang、Elisabeth HM Temme、Hugo Kesteloot

  DOI：10.1080/07315724.2001.10719060

  日期：2001.10

  Objective: Alcohol drinkers are generally considered to underreport their alcohol intake, but little is known about whether they correctly report their energy intake (EI). We assessed the validity of the reported energy intake of alcohol drinkers using the 24-hour urinary (U) excretion of potassium (K) and sodium (Na) as biomarkers.Methods: A total of 2,124 men and 1,998 women 25 to 74 years of age with a 24-hour urine collection. a random sample of the Belgian Interuniversity Research on Nutrition and Health (BIRNH), were studied. Dietary intake (D), including alcohol consumption, was assessed by a one-day food record, Basal metabolic rate (BMR) was predicted from age gender and weight. As a measure for the degree of reporting error. D-K/U-K, D-Na/U-Na, EI/U-K, Non-alcohol EI/U-Na (NAEI/U-Na), Ei/U-Na, EVU-creatinine and EI/BMR ratios were calculated and compared among non-, moderate and heavy drinkers in both genders.Results: El, NAEI and all seven ratios examined generally increased with the level of alcohol intake in both genders. After adjustment for age, body mass index, smoking and educational level, most ratios were significantly higher in moderate drinkers (p < 0.02 to p < 0.0001) and in heavy drinkers (all p < 0.0001) than in non-drinkers. These differences were most significant in male heavy drinkers. The exceptions were D-K/U-K. D-Na/U-Na and NAEI/U-Na in moderate and female heavy drinkers and EI/U-K in male moderate drinkers. The estimated amount of the overreporting of El by heavy drinkers was 27.8% in men and 13.7% in women.Conclusions: This study provides evidence that El and NAEI obtained from the BIRNH study was overreported among alcohol drinkers, especially among male heavy drinkers. It also indicates that El from alcohol replaced El from food.