2-Methoxy-1-phenyl-but-3-en-1-ol | 267663-72-9

• 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: 2-Methoxy-1-phenyl-but-3-en-1-ol
• 英文别名: 2-methoxy-1-phenylbut-3-en-1-ol
• CAS: 267663-72-9
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: AUNSCQNKFRNJAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  烯丙基甲基醚 、 苯甲醛 生成 2-Methoxy-1-phenyl-but-3-en-1-ol
  参考文献：
  名称：

  .gamma.-Alkoxyallylboronates as useful reagents for preparation of differentially protected diol derivatives

  摘要：

  DOI：

  10.1021/jo00133a059

文献信息

• Cytochrome P450-Catalyzed Hydroxylation of Mechanistic Probes that Distinguish between Radicals and Cations. Evidence for Cationic but Not for Radical Intermediates
  作者：Martin Newcomb、Runnan Shen、Seung-Yong Choi、Patrick H. Toy、Paul F. Hollenberg、Alfin D. N. Vaz、Minor J. Coon

  DOI：10.1021/ja994106+

  日期：2000.3.1

  Oxidation of the mechanistic probes trans,trans-2-methoxy-3-phenylmethylcyclopropane and methylcubane by six cytochrome P450 isozymes has been studied. The probes differentiate between radical and cationic species in that different structural rearrangements occur for the two types of intermediates. The P450 isozymes are the phenobarbital-inducible hepatic isozymes P450 2B1 (from rat) and P450 2B4 (from

  研究了六种细胞色素 P450 同工酶对反式、反式-2-甲氧基-3-苯基甲基环丙烷和甲基立方烷的氧化机制。探针区分自由基和阳离子物种，因为两种类型的中间体发生不同的结构重排。P450 同工酶是苯巴比妥诱导的肝同工酶 P450 2B1（来自大鼠）和 P450 2B4（来自兔），表达的截短同工酶 P450 Δ2B4 和 P450 Δ2E1（乙醇诱导，来自兔），以及后两者的突变体活性位点苏氨酸被丙氨酸、Δ2B4 T302A 和 Δ2E1 T303A 取代。从两个探针中都发现了阳离子重排产物。反式氧化，反式-2-甲氧基-3-苯基甲基环丙烷产生少量自由基衍生的重排产物，表明羟基化是通过插入反应发生的，过渡态寿命在 80-200 fs 范围内。细胞色素 P450 催化羟基化的机理描述符合...
• Stereoretentive introduction of (E)- and (Z)-γ-alkoxyallyl groups into carbonyl compounds via light-promoted reaction with γ-alkoxyallylstannanes
  作者：Akio Takuwa、Yutaka Nishigaichi、Seiji Ebara、Hidetoshi Iwamoto

  DOI：10.1039/a804459g

  日期：——

  The light-promoted condensation between carbonyl compounds and (E)- or (Z)-γ-alkoxyallylstannanes affords predominantly the linear homoallylic alcohols, with retention of the double bond geometry of the γ-alkoxyallyl moieties.

  羰基化合物与(E)-或(Z)-δ-烷氧基烯丙基锡之间的光促进缩合主要产生线性均烯丙基醇，并保留δ-烷氧基烯丙基分子的双键几何形状。
• Stereoselective acyclic synthesis via allylmetals: Threo vicinal diols from both - and -γ-alkoxyallyltins and aldehydes
  作者：Masato Koreeda、Yoshio Tanaka

  DOI：10.1016/s0040-4039(00)95670-3

  日期：1987.1

  Both - and -γ-alkoxyallyltins stereoselectively add to aldehydes in the presence of BF3·OEt2 at −78°C in CH2Cl2 to produce the threo (or syn) vicinal diol monoalkyl ether unit.

  两个-和-γ-alkoxyallyltins立体选择性地添加到醛在BF的存在3 ·OET 2在-78℃下在CH 2氯2以产生苏式（或顺式）邻二醇单烷基醚单元。
• Cr-catalyzed allylic C(sp3)–H addition to aldehydes enabled by photoinduced ligand-to-metal charge transfer
  作者：Xianrong Zeng、Feng-Hua Zhang、Runchen Lai、Xiaoyu Lin、Zhaobin Wang

  DOI：10.1007/s11426-023-1911-x

  日期：2024.5

  chromium (Cr) complexes as catalysts through visible-light-induced LMCT. By investigating the reaction pathway through various mechanistic studies, including radical trapping, kinetic isotope effect (KIE) analysis, and transient absorption spectroscopy, valuable insights have been gained. The proposed mechanism suggests the intermediacy of bromine radicals through homolysis of the Cr–Br bond. Notably

  光诱导配体到金属电荷转移（LMCT）已成为以可持续方式合成有机分子的有效策略。然而，现有的大多数关于通过光诱导LMCT选择性C(sp 3 )–H键功能化的报道都集中在使用后过渡金属或稀土金属进行自由基加成或交叉偶联。相比之下，利用 3d 早期过渡金属进行光诱导 LMCT 提出了重大挑战。在此，我们描述了一种前所未有的烯丙型 C(sp 3 )–H 加成醛的方法，通过可见光诱导的 LMCT 采用铬 (Cr) 配合物作为催化剂。通过自由基捕获、动力学同位素效应 (KIE) 分析和瞬态吸收光谱等各种机理研究来研究反应途径，获得了宝贵的见解。所提出的机制表明溴自由基通过 Cr-Br 键的均裂发挥中介作用。值得注意的是，该协议扩展了我们对地球丰富的铬配合物的光化学性质的理解。
• Preparation of γ-Heterosubstituted Allylindium and Diindium Reagents and Their Reactions with Carbonyl Compounds
  作者：Tsunehisa Hirashita、Toshiya Kamei、Tomoaki Horie、Hatsuo Yamamura、Masao Kawai、Shuki Araki

  DOI：10.1021/jo9816111

  日期：1999.1.1

  Various gamma-heteroatom-substituted allylindium reagents were prepared, and their reactions with carbonyl compounds were examined. The reaction of 1,3-dibromopropene with metallic indium gave two types of organoindium species, gamma-bromoallylindium and allylic diindium reagents. While the former gave 2-phenyl-3-vinyloxirane upon the coupling with benzaldehyde, the latter gave 1-phenylbut-3-en-1-o1. 1-Iodo-3-bromopropene gave the homoallylic alcohol exclusively. gamma-Alkoxyallylindium reagents were prepared by treating the corresponding gamma-alkoxyallyllithium with indium trichloride and reacted with benzaldehyde to give vic-diol mono ethers in high yields with good syn selectivity. gamma-(Trimethylsilyl)allylindium and alpha,gamma-disubstituted allylindium reagents were also prepared via transmetalation with the corresponding allyllithium.