1-(2-methylnaphthyl) methyl sulfide | 350600-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-methylnaphthyl) methyl sulfide
• 英文别名: methyl(2-methylnaphthalen-1-yl)sulfane；Methyl 2-methyl-1-naphthyl sulfide；2-methyl-1-methylsulfanylnaphthalene
• CAS: 350600-29-2
• 化学式: C₁₂H₁₂S
• 分子量: 188.293
• InChiKey: WUVZODZFFCVEAB-UHFFFAOYSA-N

物化性质

• 沸点：
  306.8±21.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-methylnaphthyl) methyl sulfide 在 间氯过氧苯甲酸 作用下， 以 氯仿 、 水 为溶剂， 反应 1.0h， 生成 1-(Methylsulfinyl)-2-methylnaphthalene
  参考文献：
  名称：

  Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution

  摘要：

  Barriers for the EZ interconversion of atropisomers of 1-naphthyl sulfoxides (ArSOR) having a methyl group at position 2 of the naphthalene moiety were measured by variable-temperature NMR. Their values were found to cover the range 10.6-18.4 kcal mol-1, the extreme values corresponding to derivatives 1 (R = Me) and 4 (R = Bu(t)), respectively. NOE and LIS measurements indicated that the Z atropisomer is more stable than the E but that the absence of the methyl group at position 2 of the naphthalene moiety reverses this trend, rendering E more stable than Z. Solid-state NMR and X-ray diffraction of 4 established that only the more stable atropisomer (Z) is present in the crystalline state. Molecular mechanics calculations suggest that the Z,E interconversion process might occur by a rotation pathway having an opposite direction in the case of the more hindered derivatives 3 and 4 (R = Pr(i) and Bu(t), respectively) with respect to the less hindered 1 and 2 (R = Me and Et, respectively). The enantiomers, which are due to the presence of the asymmetric sulfur atom, were resolved on a chiral stationary phase (DACH-DNB) having an SS configuration. Asymmetric oxidation reactions were employed to assign the absolute R configuration to the more retained enantiomers of alkyl aryl sulfoxides. The opposite trend (S being retained longer) was observed for diaryl sulfoxides such as 5 (R = Ph). In the case of the derivative with the largest interconversion barrier, sulfoxide 4, it was also possible to resolve (at -35-degrees-C) the two enantiomeric forms and their associated atropisomers. The use of on-line CD detection and the knowledge of the NMR assignments allowed us to unambiguously assign the elution order of the four species as ES, ER, ZS, ZR.

  DOI：

  10.1021/jo00073a028
• 作为产物：
  描述：

  二甲基亚砜 、 alkaline earth salt of/the/ methylsulfuric acid 在 zinc(II) fluoride 、 copper(I) bromide 作用下， 反应 36.0h， 生成 1-(2-methylnaphthyl) methyl sulfide
  参考文献：
  名称：

  通过C–S键裂解， 镍催化的芳基硫醚与烷基格氏试剂的交叉偶联†

  摘要：

  提出了镍催化的芳基硫醚与烷基格氏试剂的交叉偶联，同时伴随着C（芳基）–SMe键的裂解。该方法的特点是温和的条件和适度的官能团耐受性（例如羟基，卤素和杂环），这应可直接实现对含硫分子的修饰。

  DOI：

  10.1039/c8cc03665a

文献信息

• Peri-Selective Direct Acylmethylation and Amidation of Naphthalene Derivatives Using Iridium and Rhodium Catalysts
  作者：Yuji Nishii、Masahiro Miura、Chandrababu Naidu Kona、Rikuto Oku

  DOI：10.1055/a-1472-1059

  日期：2021.9

  An iridium-catalyzed acylmethylation and a rhodium-catalyzed amidation of naphthalene derivatives are reported, adopting sulfoxonium ylides and dioxazolones as carbene and nitrene transfer agents, respectively. The use of SMe group as a directing group was key to ensure the peri-selective functionalization, and it can be easily removed or diversely transformed to other synthetically useful functionalities

  据报道，萘衍生物的铱催化的酰基甲基化和铑催化的酰胺化，分别采用了亚砜基和二恶唑酮作为卡宾和腈转移剂。使用SMe基团作为导向基团是确保peri-selective功能化的关键，并且在催化后，它可以轻松除去或多样化地转化为其他合成有用的功能。
• Determination of Absolute Configuration Using Vibrational Circular Dichroism Spectroscopy:  The Chiral Sulfoxide 1-(2-methylnaphthyl) Methyl Sulfoxide
  作者：P. J. Stephens、A. Aamouche、F. J. Devlin、S. Superchi、M. I. Donnoli、C. Rosini

  DOI：10.1021/jo001403k

  日期：2001.6.1

  We report the determination of the absolute configuration (AC) of the chiral sulfoxide, 1-(2-methylnaphthyl) methyl sulfoxide, 1, using vibrational circular dichroism (VCD) spectroscopy. The VCD of 1 has been measured in the mid-IR spectral region in CCl(4) solution. Analysis employs the ab initio DFT/GIAO methodology. DFT calculations predict two stable conformations of 1, E and Z, Z being lower in

  我们报告使用振动圆二色性（VCD）光谱测定手性亚砜1-（2-甲基萘基）甲基亚砜1的绝对构型（AC）。1的VCD已在CCl（4）解决方案的中红外光谱区域中测量。分析采用从头算DFT / GIAO方法。DFT计算预测1，E和Z的两个稳定构型，Z的能量比E低<1 kcal / mol。在这两个构象中，SO键从与萘基部分的共面旋转了30-40度。两种构型的平衡混合物的预测的非偏振吸收（“ IR”）光谱允许在中红外光谱区域中分配实验性红外光谱。E和Z构象的存在是显而易见的。
• CHROMENE COMPOUND AND CURABLE COMPOSITION
  申请人：TOKUYAMA CORPORATION

  公开号：US20140225050A1

  公开（公告）日：2014-08-14

  A chromene compound which has a sulfur-containing substituent represented by the following formula (2) at the 6-position and/or 7-position carbon atom of an indeno (2,1-f)naphtho(1,2-b)pyran structure and is excellent in photochromic properties and stability at a high temperature. (In the above formula, ring X is an aromatic hydrocarbon ring or aromatic heterocyclic ring, R 3 and R 4 are each independently an alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, amino group, heterocyclic group containing a ring member nitrogen atom and bonded to the ring X bonded thereto via the nitrogen atom, halogen atom, aryloxy group or aryl group, and “a” is an integer of 0 to 4.)

  一种含有硫取代基的色烯化合物，其在indeno（2,1-f）naphtho（1,2-b）pyran结构的6-位和/或7-位碳原子处，用以下式子（2）表示，并且具有优异的光致变色性能和高温稳定性。（在上述式子中，环X是芳香族烃环或芳香族杂环环，R3和R4各自独立地是烷基，卤代烷基，环烷基，烷氧基，氨基，含有环成员氮原子并通过氮原子与环X结合的杂环基，卤素原子，芳氧基或芳基，而“a”是0到4的整数。）
• Bifunctional 1-Hydroxypyrene Photocatalyst for Hydrodesulfurization via Reductive C(Aryl)–S Bond Cleavage
  作者：Di Wu、Akira Shiozuka、Kyohei Kawashima、Toshifumi Mori、Kohei Sekine、Yoichiro Kuninobu

  DOI：10.1021/acs.orglett.3c01061

  日期：2023.5.12

  stoichiometric amounts of metal reagents. Detailed mechanistic studies based on control experiments, spectroscopic measurements, and computational studies revealed that the cleavage of the C(aryl)–S bond and the formation of the C(aryl)–H bond proceeded via the formation of the ion pair between the radical anion of alkyl aryl thioether and Et3N+H, resulting in the generation of a sulfur radical. In addition

  我们使用 1-羟基芘作为 Brønsted 酸还原剂双功能光催化剂，通过 C(芳基)-S 键的还原裂解，开发了可见光诱导的烷基芳基硫醚加氢脱硫。加氢脱硫反应在简单的反应条件下进行（1-羟基芘和Et 3紫色 LED 照明下 THF 中的 N）；该反应不需要通常用于加氢脱硫的化学品，例如氢硅烷、过渡金属催化剂和/或化学计量的金属试剂。基于对照实验、光谱测量和计算研究的详细机理研究表明，C(芳基)-S 键的裂解和 C(芳基)-H 键的形成是通过自由基之间离子对的形成进行的烷基芳基硫醚和Et 3 N + H的阴离子，导致硫自由基的产生。此外，1-羟基芘催化剂通过氢原子转移 (HAT) 从 Et 3 N再生。
• US8916071B2
  申请人：——

  公开号：US8916071B2

  公开（公告）日：2014-12-23