dl-benzhydrol-2,3,4,5,6-d5 | 99398-35-3

• 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: dl-benzhydrol-2,3,4,5,6-d5
• 英文别名: pentadeuterophenyl-phenyl-methanol；benzhydrol-2,3,4,5,6-d₅；benzhydrol-D₅；<2,3,4,5,6-D5>Diphenylmethanol；pentadeuteriophenyl-phenyl-methanol；Benzhydrol-d5；(2,3,4,5,6-pentadeuteriophenyl)-phenylmethanol
• CAS: 99398-35-3
• 化学式: C₁₃H₁₂O
• 分子量: 189.198
• InChiKey: QILSFLSDHQAZET-DYVTXVBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dl-benzhydrol-2,3,4,5,6-d5 在 Pd-BaSO₄ 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、399.99 kPa 条件下， 反应 36.0h， 以90%的产率得到1-benzylbenzene-2,3,4,5,6-d₅
  参考文献：
  名称：

  Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane)

  摘要：

  AbstractTwo distinct proton exchange reactions occur in metastable gaseous benzylbenzenium ions, generated by isobutane chemical ionization of diphenylmethane and four deuterium‐labelled analogues. Whereas the proton ring‐walk at the benzenium moiety is fast giving rise to a completely random intraannular proton exchange, the interannular proton exchange is surprisingly slow and competes with the elimination of benzene. A kinetic isotope effect of kH/kD= 5 has been determined for the interannular proton transfer, and a particularly high energy barrier of 50–75 kJ mol−1 has been estimated. These observations are attributed to steric restrictions of the ring‐to‐ring proton transfer in benzylbenzenium ions and contrasted to the fast interannular proton exchange in the higher homologues.

  DOI：

  10.1002/oms.1210210802
• 作为产物：
  描述：

  (+)-4'-nitrobenzhydrol-2,3,4,5,6-d5 在 palladium on activated charcoal 盐酸 、 氢气 、 次磷酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， -5.0~25.0 ℃ 、101.33 kPa 条件下， 反应 72.17h， 生成 dl-benzhydrol-2,3,4,5,6-d5
  参考文献：
  名称：

  Chiral benzhydrol-2,3,4,5,6-d5

  摘要：

  DOI：

  10.1021/jo00225a067

文献信息

• Reactions and Mechanistic Studies of Rhenium-Catalyzed Insertion of α,β-Unsaturated Carbonyl Compounds into a C–H Bond
  作者：Yoichiro Kuninobu、Yuta Nishina、Kayo Okaguchi、Makoto Shouho、Kazuhiko Takai

  DOI：10.1246/bcsj.81.1393

  日期：2008.11.15

  A rhenium complex, [ReBr(CO) 3 (thf)] 2 , catalyzes the insertion of α,β-unsaturated carbonyl compounds into a C-H bond of aromatic compounds having nitrogen-containing directing groups. In this reaction, Re 2 (CO) 10 can also be used as a catalyst. When imines are employed as the aromatic substrates, sequential cyclization proceeds and indene derivatives are obtained in good to excellent yields. This

  铼络合物[ReBr(CO) 3 (thf)] 2 催化α,β-不饱和羰基化合物插入具有含氮导向基团的芳族化合物的CH键中。在该反应中，Re 2 (CO) 10 也可用作催化剂。当使用亚胺作为芳族底物时，顺序环化进行，并以良好至极好的产率获得茚衍生物。这种反应性与钌和铑配合物的反应性相反，钌和铑配合物通常用作不饱和分子插入 CH 键的催化剂。对反应机理的研究表明，铼催化剂促进了芳香族化合物的 CH 键活化，α,β-不饱和羰基化合物插入 Re-C 键，
• Synthesis of<i>ortho</i>-Acylphenols through the Palladium-Catalyzed Ketone-Directed Hydroxylation of Arenes
  作者：Fanyang Mo、Louis J. Trzepkowski、Guangbin Dong

  DOI：10.1002/anie.201207479

  日期：2012.12.21

  Ketone in charge: A formal ketone‐directed palladium‐catalyzed ortho‐hydroxylation of arenes has been developed as an effective approach to access o‐acylphenols from simple arylketones. A Pd‐catalyzed oxidative ortho‐carbonylation reaction using ketone directing groups to access a ketal–lactone motif is also demonstrated. The ubiquity and versatile nature of ketones make these methods attractive. BTI=PhI(TFA)2;

  负责的酮：已开发出正式的酮导向的钯催化芳烃的邻羟基化反应，作为从简单的芳基酮中获得邻酰基苯酚的有效方法。还显示了使用酮引导基团访问缩酮-内酯基序的Pd催化的氧化邻位羰基化反应。酮的普遍性和通用性使这些方法具有吸引力。BTI = PhI（TFA）2；DCE = 1,2-二氯乙烷
• Co(III)-Catalyzed Synthesis of Quinazolines via C–H Activation of <i>N</i>-Sulfinylimines and Benzimidates
  作者：Fen Wang、He Wang、Qiang Wang、Songjie Yu、Xingwei Li

  DOI：10.1021/acs.orglett.6b00227

  日期：2016.3.18

  as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.

  芳烃的C–H活化已被确定为通过芳烃与不饱和偶联伙伴之间的环化进行杂环合成的重要策略。然而，腈未能充当这样的偶联伴侣。二恶唑酮已被用作腈的合成子，并且随后与带有功能性导向基团的芳烃如N-亚磺酰亚胺和苯甲二胺偶合，提供了在Co（III）催化下容易接近两类喹唑啉的途径。
• REACTIONS OF BENZENE VAPOR-CALCIUM ATOM WITH ORGANIC HALIDES AND CARBONYL COMPOUNDS
  作者：Kunio Mochida、Hidenori Takeuchi、Yoo Hiraga、Hiroyasu Ogawa

  DOI：10.1246/cl.1984.1989

  日期：1984.11.5

  Reactions of benzene vapor-calcium atom with organic halides and carbonyl compounds were examined. Benzene vapor-calcium atom reacted with organic halides (RX) to give phenyl-substituted products (PhR) and reduced products (RH). The reactions of benzene vapor-calcium atom with ketones (RR′CO) or benzaldehyde gave two kinds of alcohol PhRR′COH and RR′CHOH, or Ph2CHOH and PhCH2OH, respectively

  研究了苯蒸气-钙原子与有机卤化物和羰基化合物的反应。苯蒸气-钙原子与有机卤化物 (RX) 反应生成苯基取代产物 (PhR) 和还原产物 (RH)。苯蒸气-钙原子与酮（RR'CO）或苯甲醛反应生成两种醇PhRR'COH和RR'CHOH，或Ph2CHOH和PhCH2OH
• Base‐Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
  作者：Debabrata Maiti、Atreyee Halder、Suman De Sarkar

  DOI：10.1002/adsc.201900995

  日期：2019.11.5

  transition metal‐free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2‐iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C−N bond formation followed by a radical C−C coupling in a cascade sequence. The used base potassium tert‐butoxide plays a dual role in dehydrogenation

  目前的方案代表了从苯甲醛和2-碘苯胺衍生物等丰富的原料中无过渡金属合成多取代菲啶的方法。该反应涉及依次进行的醇氧化和与胺的直接缩合反应，形成C-N键，然后以级联顺序进行自由基C-C偶联。使用的碱式叔丁醇钾在脱氢和均相芳族取代反应中起双重作用。使用这种方法，合成了二十种取代的菲啶衍生物，分离产率高达85％。